Vacation Rentals By Owner In Hillsdale, NY

$356.76

Saltbox-style residence in the Berkshires

Hillsdale, New York, United States

brDiscover the allure of this enchanting Saltbox-style residence nestled in the picturesque town ofbrHillsdale, NY. With three stories of charm and character, this house seamlessly blends comfort and style to create an inviting retreat. Accommodating up to 8 people, the three bedrooms boast queen-size beds, complemented by a sleeper couch in the basement for added flexibility. Both bathrooms, located on the main and top floors, feature relaxing bathtubs.brbrThe basement transforms into an entertainment haven, offering a perfect escape with a TV and abrping pong table for friendly competitions and leisurely evenings.brbrStep outside onto the patio, where a generously sized table and comfortable outdoor seating beckonbryou to savor al fresco meals or simply unwind in the fresh country air. Beyond the patio, the propertybrextends its charm with access to the serene Green River.brbrConveniently located just a short drive from Great Barrington, a charming town renowned for itsbrgreat shops and delectable dining options, the house also sits a mere 40 minutes away from the vibrant town of Hudson. During the summer months, guests can immerse themselves in a rich tapestry of cultural offerings, from concerts at Tanglewood to plays at Shakespeare and Co in Lenox, or captivating dance performances at Jacob’s Pillow. brbrOutdoor enthusiasts will appreciate the proximity to activities like hiking the Appalachian Trail and enjoying a refreshing swim in a local lake.brbrFor those enchanted by winter's embrace, nearby ski slopes provide the perfect playground forbrwinter enthusiasts. Whether you seek relaxation or adventure, this house offers a retreat in every season.br

3

Bed

2

Bath

6

Sleeps

$490.5

/ Nightly

Private Vacation Home

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Hillsdale, New York, United States

Spring is quiet up here. Wildflowers push through across six private acres, the trails at Catamount and Bash Bish Falls are opening back up, and the Berkshire ridgeline turns green before anywhere else in the valley. No crowds. Just mountain air, birdsong from the porch, and the kind of silence that makes you realize how loud everything else has been.brbrMeadow View Manor is a four-bedroom Post and Beam retreat perched high on a Hillsdale hillside — the perfect base for a spring hiking weekend, or for plugging in your laptop and working remotely for a week with 500+ Mbps fiber WiFi and mountain views outside every window. The Copake-Hillsdale Farmers Market opens in May, Hawthorne Valley Farm is ten minutes away, and the wildflower bloom along the South Taconic Trail is worth the drive alone.brTwo hours from Midtown Manhattan. Two and a half from Boston. Five minutes from Catamount. And a world away from all of it.brbrTHE HOUSEbrbrThree levels, 3,072 square feet, each floor with its own purpose.brbrTOP LEVEL — SLEEPbrFour bedrooms, all on the top floor for quiet and privacy. Two master suites: one with a private en-suite bathroom (walk-in shower, hair dryer, fresh towels and linens), the other sharing a full bathroom with the remaining two bedrooms. A half bath on the main level means no morning traffic jams.brbrEvery bedroom has its own whisper-quiet mini-split for individual heating and cooling — no fighting over the thermostat. Set your room to exactly the temperature you want.brbrBeds: one king, two queens, and two twins. Sleeps eight comfortably. All linens, pillows, and towels are provided and freshly laundered for every stay.brbrMAIN LEVEL — GATHERbrThe heart of the house. The kitchen was fully remodeled in 2025 — quartz countertops, Samsung electric range with five burners and a warming zone, Samsung oven, full-size refrigerator, dishwasher, microwave, and range hood. It's stocked with everything you need to cook real meals: pots, pans, knives, cutting boards, mixing bowls, a Keurig Duo coffee maker (pods or a full 12-cup carafe), coffee grinder, tea kettle, blender, toaster, ice maker, wine opener, plates, glasses, silverware — the works. If you're wondering whether we have it, we probably do. And if we don't, just ask before your trip and we'll have an answer.brbrThe kitchen flows into an eating area, a formal dining room, and an open living space anchored by a wood-burning fireplace. There's nothing quite like lighting a fire after a day on the trails or the slopes and sinking into the couch while the mountain goes dark outside.brbrThe living area has a smart TV with access to all major streaming services — just log in with your account. Three full-size patio doors open onto the veranda overlooking the mountain. This is where mornings happen, where afternoon reading happens, where dinner conversations drift into the evening. Outside, a deck with a table, chairs, and a BBQ grill is set up and ready for al fresco cooking with a view.brbrLOWER LEVEL — PLAYbrAn open-concept game room with a ping-pong table, a second smart TV, and a sofa bed that adds extra sleeping capacity for larger groups. Board games are stacked and ready — Monopoly, Trivial Pursuit, and more. Books line the shelves if you'd rather go quiet.brbrWalk out from here through sliding glass doors onto a large ground-level wooden deck. This is where the fire pit lives. Pull up a chair, light a fire, and look up — on a clear night you can trace the Milky Way from one horizon to the other. The east-facing mountain view makes this one of the best stargazing spots in the region.brbrBUILT FOR REMOTE WORKbrbrThis isn't decent WiFi. Meadow View Manor runs on fiber-optic internet with an Orbi 860 Series Tri-Band WiFi 6 mesh network delivering 500+ Mbps to every corner of the house — upstairs, downstairs, out on the veranda. That's enough bandwidth for simultaneous video calls on Zoom or Teams, 4K streaming in the living room, and large file uploads from the desk, all at the same time without a hiccup.brbrA dedicated desk and ergonomic chair are set up and ready for a real work session — not a kitchen counter with bad lighting.brbrCell service is limited this far up the mountain. The fiber connection is your lifeline, and it's rock solid. If you're looking to work remotely for a week or a month with panoramic mountain views outside your window instead of a cubicle wall, this is the setup you've been searching for. Extended stays welcome — reach out for weekly and monthly rates.brbrTHE LANDbrbrSix private acres of Berkshire mountainside. The property sits at the end of a winding country road — no through traffic, no passing cars, no noise. When you step outside, you'll hear wind moving through the trees, birdsong in the morning, and crickets at night. That's it.brbrThe east-facing mountain views are expansive — rolling meadows giving way to forested ridgelines. Mornings here are special: sunrise paints the valley in golds and pinks before the rest of the world wakes up. Evenings are just as good, with the mountain silhouette darkening against a sky that gets clearer and more star-filled the later you stay out.brbrDeer wander through the property regularly. Hawks circle overhead. The occasional fox crosses the meadow at dusk. This is genuine countryside — not a subdivision with a nature theme.brbrWHAT'S NEARBYbrbrThe location hits a rare sweet spot — remote enough to feel like a real escape, close enough that nothing is far when you want it.brbrOutdoor Adventures:brbrCatamount Ski Area and Aerial Adventure Park — 5 min drivebrbrCopake Lake — 10 min (kayak and canoe rentals, swimming, Copake Country Club for golf)brbrBash Bish Falls — 20 min (Massachusetts' tallest waterfall at 60 feet, with trails from the NY side through Taconic State Park)brbrSouth Taconic Trail — trailhead minutes from the house, 12 miles of ridgeline hiking with summit viewsbrbrTaconic State Park — 20 min (camping, Harlem Valley Rail Trail for biking)brbrSki Butternut — 25 minbrbrJiminy Peak Mountain Resort — 50 minbrbrFood, Culture, and Towns:brbrHawthorne Valley Farm and Market — 10 min (organic produce, artisan cheese, fresh bread)brbrCopake-Hillsdale Farmers Market — seasonal, just down the roadbrbrHudson — 25 min (Warren Street galleries, farm-to-table restaurants, antique shops, craft cocktail bars)brbrGreat Barrington — 25 min (restaurants, Berkshire Co-op Market, shopping, live music)brbrTanglewood — 40 min (summer home of the Boston Symphony Orchestra)brbrLocal wineries, breweries, and cideries throughout the valleybrbrGetting Here:brbr2 hours from Midtown Manhattan via Taconic State Parkwaybrbr2.5 hours from Bostonbrbr9 minutes to the Taconic Parkway entrancebrbrAmtrak Hudson station — 30 min (direct service to/from NYC Penn Station)brbrThe drive up is part of the experience. Once you turn off the Taconic, the roads narrow, the trees close in, and by the time you reach the winding road to the house, you've already started to decompress.brbrPERFECT FORbrbrFamilies looking for space — three levels means kids can play in the game room while adults relax upstairsbrbrFriend groups and reunions — eight beds, a big kitchen, a dining room, and a fire pit that keeps the night goingbrbrCouples traveling together — two master suites with real privacy between thembrbrRemote workers — fiber WiFi, a real desk, and the kind of quiet that makes deep work actually possiblebrbrDog owners — six open acres for your pups to explore (up to two dogs welcome; no cats)brbrSki weekends — five minutes to Catamount, twenty-five to Butternut, fifty to Jiminy PeakbrbrHoliday gatherings — Thanksgiving around the dining table, New Year's Eve by the fireplacebrbrDOGS WELCOMEbrbrUp to two dogs are welcome on the property and across all six acres. There's no fencing, so please keep an eye on them outdoors. The meadows and wooded edges are a dog's paradise — just watch for deer (they're curious but keep their distance). No cats, please.brbrTHE DETAILSbrbrFiber internet — Orbi 860 Tri-Band WiFi 6 mesh, 500+ Mbps, every room coveredbrbrClimate — Mini-split inverter AC and heat in every bedroom and on every main floor, plus a propane heating systembrbrFireplace — Wood-burning, stocked and readybrbrFire pit — Ground-level deck, evenings under the starsbrbrKitchen — Fully remodeled 2025, quartz countertops, fully stocked (see above)brbrLaundry — GE high-capacity washer and dryer, detergent providedbrbrSmart TVs — On every level, all major streaming apps installed (bring your login)brbrParking — Driveway directly next to the house, room for multiple carsbrbrSafety — Smoke detectors on every level, carbon monoxide detectors, fire extinguisher, first aid kit, deadbolt locks, exterior lightingbrbrBaby gear — Travel crib available on requestbrbrLinens and towels — Provided and freshly laundered, including bath towels, hand towels, and washclothsbrbrToiletries — Shampoo, basic soaps, toilet paper, paper towels providedbrbrPRICING AND FEESbrbrOur prices include all fees. No hidden charges, no surprise cleaning fees, no service fee markups. What you see is what you pay.

4

Bed

2

Bath

8

Sleeps

$662.67

/ Nightly

Private Vacation Home

Lake Front House with Rustic and Charming Feel

Hillsdale, New York, United States

Welcome to your perfect escape on beautiful Copake Lake! Nestled in the heart of New York`s Hudson Valley, our cozy and inviting lakefront home offers the ideal blend of relaxation and adventure. Whether you`re sipping coffee on the deck, kayaking at sunrise, or gathering around the firepit under the stars, this is where unforgettable memories are made.brbrThe Hideaway at Hillsdale|Lakefront Retreat on Copake Lake|Dock, Kayaks & Sunset ViewsbrbrWelcome to the Hideaway at Hillsdale – a newly renovated, family-friendly lakefront retreat on beautiful Copake Lake in New York’s Hudson Valley. Whether you’re enjoying sunrise paddles, sunset cocktails on the deck, or cozy nights around the firepit, this peaceful getaway is designed for relaxation, reconnection, and fun. brbrThe Spacebr• 3 Bedroomsbr Bedroom 1: King-size bedbr Bedroom 2: Queen-size bedbr Bedroom 3: Queen-size bed + one full-size bedbr(Comfortable sleeps 8)brbr• 1.5 BathroomsbrbrLakefront LivingbrStep out the back door to your private dock and enjoy direct access to Copake Lake. Spend your days kayaking, swimming, or simply soaking up the views from the shoreline.brbrOutdoor OasisbrThe large deck is perfect for outdoor dining, morning coffee, or sunset watching. In the evening, gather around the firepit or fire up the grill for a lakeside cookout. brbrComfort & Conveniencebr• Fully equipped kitchenbr• Air-conditioningbr• Wi-Fibr• Smart TVbrbrWhy You’ll Love Itbr• Tranquil, scenic lakefront settingbr• Breathtaking sunsets over the lakebr• Ideal for families, reunions, or small group getawaysbr• Quiet, peaceful location just minutes from local attractionsbrbrLocation HighlightsbrClose to hiking trails, golf at Copake Country Club, skiing at Catamount, and charming towns like Hudson and Great Barrington.brbrPlan your perfect lakeside escape – your Copake Lake adventure awaits!brbrTucked away on a private road, our home offers a calm retreat in a quiet neighborhood.brbrDisclaimers:brbr-Cancellation Policy:brWe strictly follow the cancellation policy selected at booking. Airbnb offers travel insurance, which we recommend if you’re concerned about unexpected events.brbr-Alterations:brReducing nights from your reservation is subject to the cancellation policy and may not be approved. Extensions are almost always welcome, though last-minute requests may require cleaner confirmation.brbr-Regular Maintenance:brEssential services, such as lawn care, snow removal, pool/hot tub cleaning (where applicable), and pest control, may occur during your stay. These vendors follow a regular schedule, though days and times can vary slightly. We kindly ask that you allow them to complete their work quickly so you can enjoy the rest of your day.brbr-Damage:brIf something is damaged, please let us know right away. We value honesty and will work with you to find a fair resolution, whether the damage is minor or significant.brbr-Wildlife:brOur homes are often in rural areas, so you may encounter insects (bees, spiders, flies), small animals (squirrels, raccoons), and occasionally larger wildlife (deer, bears). Please be prepared for nature during your stay and remember they’re more afraid of you than you are of them. brbr-Power & Internet Outages:brOutages can happen in this area due to weather or other factors. Because they are out of our control, we do not provide refunds for these interruptions, but we’ll do our best to help you work around them. brbr-Weather:brRain, wind, snow and extreme heat and humidity are possible depending on the season. Please plan your travel accordingly, as we cannot refund missed stays due to weather conditions preventing travel. brbr-Additional Guests & Occupancy Limits:brThe listed occupancy applies to your entire stay, not just overnight guests. Any extra guests or events must be approved in writing before arrival. Unapproved gatherings or over-occupancy will result in immediate removal without a refund.brbr-Pools, Hot Tubs & Outdoor Amenities:brThese features may be seasonal. If your booking is at the beginning or end of the season and you’re concerned, check with us to confirm availability.brbr-Mail & Packages:brYou may have mail or packages delivered during your stay, but please ensure they arrive while you are present and are clearly addressed with your name.

Bed

Bath

Sleeps

$309.28

/ Nightly

Private Vacation Home

Charming 3-bedroom house with AC, WiFi in quaint Hillsdale

Hillsdale, New York, United States

Get a taste of the Upstate life snug in the foothills of the Berkshires. In the quaint village of Hillsdale you are 10 minutes to Catamount, 20 minutes to Great Barrington, 30 minutes to Hudson and everywhere else in the Eastern Hudson River Valley. This family oriented house is the perfect spot for a getaway.brbrThis is a 3 bedroom home with 2 full baths that can sleep up to 7. The primary bedroom has a king bed with an attached bathroom with a walk in shower. The second bedroom has a queen bed - both of these bedrooms also have large desks providing great workspace if you need to work during your stay. The third bedroom is perfect for kids with a bunk bed and trundle providing space for 3 to sleep comfortably. There are plenty of toys in the kid's room, and games, puzzles, and books for kids and adults to enjoy! We also provide a pack n play and high chair for your little one.brbrYou will be provided a code to use for self check-in entry via a keypad lock.brbrPlease note that this is our family's weekend and summer getaway. You have full use of everything that we have in the house, but please respect our things.brbrWasher and dryer is available for your use in the unfinished basement. All other rooms are on the main level.

Bed

Bath

Sleeps

$242.67

/ Nightly

Cabin

Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale, New York, United States

Tory Hill cabin is located at seven minutes from the Taconic State Park in Copake Falls and four minutes from Catamount Ski (aereal adventure park) Mountain. The park offers several fun activities like: walking to Bash Bish Falls, biking and walking in the Rail Trail, swimming at the Ore Pit, and visiting the old Iron Works Museum. brThe cottage has a screened-in-porch, two bedrooms with a queen bed each, and the living-room has a pull-out sofa. There is plenty of outdoor space, with a tent friendly yard for fun family time!, and it is located in a quiet and private location. brbrVERY IMPORTANT!brPlease bring extra paper towels, toilet tissue, trash bags, detergent and kindling. br

Bed

Bath

Sleeps

$388.8

/ Nightly

Private Vacation Home

Hillsdale home with Stunning Views. Dog friendly!

Hillsdale, New York, United States

The views from this home are unique. The property is perched on a small hill looks out on conservancy land, as well as the Taconic Range. Former guests have commented that bind in the house is This a serene area with plenty of opportunities to spend time outside. This neighborhood is aHillsdale is close to great shopping, fantastic farmer's markets, the arts and many choices for live performances. 25 min each to Great Barrington and Hudson. This house offers the feeling that you are outside, even when you are in.. Every room has an abundance of large windows and sliders, each with a unique and beautiful view all their own. The wrap around deck is on 2 sides of the house and hosts a hot tub and relaxing outdoor furniture, including a dining table with umbrella and an outdoor couch. Listen to Taconic Creek below us, wind moving the leaves on trees, and birds doing their thing. brIf you have questions, feel free to ask through the app. Happy to answer. Best of luck in your search for the perfect place.

Bed

Bath

Sleeps

$284.44

/ Nightly

Apartment

The Brooks Motel: Exceptional Suite

Hillsdale, New York, United States

Summary:brbrWelcome to The Brooks Motel, this is a recently renovated motel located 2 minutes from Catamount, 15 mins from Downtown Great Barrington & 20 mins from Hudson NY. Think cozy beds that give you the best ZZZs, Fast WiFi, & social media-worthy views that rack up the likes.brbrbrbrThe Space:brbrWe're dishing out some serious perks at our modern Hillsdale motel. Think top-notch amenities tailored for today's jet-setters. brbrbrbrGet Ready ForbrbrModern Digs: custom made everything, desk with built-in bench, headboard with USB outlets, painted concrete floors, refreshed bathroom, and newly designed vanity area with sleek mirror and small fridge. brbrbrbrBest ZZZs: One king size bed plus one queen pull out sofa both with high quality memory foam mattresses, two different size down alternative pillows, luxurious 100% cotton linens and custom made towels. brbrbrbrBrew Break & Beyond: Fuel up whenever you please with a handy in-room coffee pot, and gear up with a hair dryer and iron for looking sharp while on the go!brbrbrbrFast Wi-Fi: Stay connected without a hitch – perfect for sharing your vacay snapshots and staying in the loop.brbrbrbrBrookside Chill: The tranquil waters of the Roeliff Jansen Kill run through the 4 acre property. The river has a nice swimming and fishing hole and trout for catch and release!brbrbrbrPet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.brbrbrbrEasy Access: Park like a pro with our hassle-free parking, so you're all set to hit the road when adventure calls. One parking spot is included in your rental. brbrbrbrSupporting Local: Expertly designed and furnished by a local third generation textile maker, Tillett Textiles, including our hand printed wallpaper, vintage art and towels. brbrbrbrSave Dough $$: helping to keep your costs down by not having daily housekeeping & there’s no front desk. You’ll be able to check yourself in as you wish. Keep it simple, keep it savvy.brbrbrbrGuest Access:brbrNeed us A quick call or text, and we're on it!brbrbrbrOther Things to Note:brbrSave Dough $$: helping to keep your costs down by saving from not having daily housekeeping & there won’t be a front desk to check in you in but we’ll provide a door code you can check yourself in as you wish. Keep it simple, keep it savvy. brbrbrbrNeed us A quick call or text, and we're on it! brbrbrbrTraveling together Depending on what layout you reserved, our rooms can sleep 1 to 6 guests, have a larger group We also rent an onsite 5 bedroom house you may be able to reserve!

1

Bath

4

Sleeps

$607.74

/ Nightly

Private Vacation Home

Hudson Valley Meets Berkshires. Modern Vacation Home w/ Upscale Comforts

Hillsdale, New York, United States

Escape to this stylish Hillsdale retreat — a beautifully renovated mid-century home with a cozy wood-burning fireplace, projector for movie nights, and inviting outdoor fire pit. Close to the Berkshires and Hudson Valley favorites, this peaceful getaway is perfect for couples, families, and friends looking to relax, recharge, and enjoy nature in every season.brbrWelcome to your modern Hillsdale retreat — a beautifully renovated mid-century home designed for cozy escapes, relaxed gatherings, and effortless Hudson Valley living.brbrInside, you’ll find warm, thoughtfully styled spaces that blend clean modern design with inviting comfort. The living room is the heart of the home, featuring a wood-burning fireplace and projector setup — perfect for slow mornings, movie nights, or unwinding after a day of exploring.brbrStart your mornings with coffee surrounded by nature. Spend your days hiking nearby trails, exploring charming Hudson Valley towns, or heading into the Berkshires for dining, shopping, and culture. In the warmer months, enjoy long evenings outside by the fire pit. In cooler seasons, cozy up indoors with a fire and a film.brbrThe home is designed to feel easy and welcoming, whether you're cooking a simple breakfast or sharing a relaxed dinner together. Clean lines, natural light, and curated details create a calm, boutique-style atmosphere that makes it easy to settle in and stay awhile.brbrThis is boutique hospitality with heart — professionally managed, thoughtfully stocked, and designed so you can focus on slowing down and enjoying your time away.brbrPerfect for couples, families, or small groups, this retreat offers the ideal balance of privacy, comfort, and proximity to everything the Hudson Valley and Berkshires have to offer.brbrOUTDOOR LIVING AT ITS BESTbrbr• Fire pit for evenings under the starsbr• Peaceful natural setting surrounded by treesbr• Outdoor space for relaxing and gatheringbr• Easy access to nearby hiking and naturebrbrINSIDE, ENJOY:brbr• Cozy living room with wood-burning fireplacebr• Projector setup for movie nightsbr• Fully equipped kitchen for easy mealsbr• Bright, modern mid-century designbr• Comfortable bedrooms for restful sleepbr• Fast WiFi for remote work or streamingbr• Clean, thoughtfully styled interiorsbrbrWhen adventure calls, you’re just minutes to Hudson Valley towns, hiking trails, local farms, and a short drive to the Berkshires for restaurants, culture, and seasonal events. Whether you're here for a summer escape, fall foliage, or a cozy winter weekend, this home is the perfect base for exploring — and an even better place to unwind.brbrPerfect For:brbr• Weekend getaway travelers escaping the citybr• Couples seeking a cozy, design-forward retreatbr• Families and small groupsbr• Guests looking for Hudson Valley + Berkshires accessbr• Remote workers wanting a peaceful, inspiring settingbrbrReady to Unwind brbrCozy, design-forward homes in Hillsdale book quickly — especially those with fireplaces and outdoor space. Secure your dates now and start planning slow mornings, fireside evenings, and a truly relaxing Hudson Valley stay.

Bed

Bath

Sleeps

$275.55

/ Nightly

Apartment

The Brooks Motel: Exceptional Suite

Hillsdale, New York, United States

Summary:brbrWelcome to The Brooks Motel, this is a recently renovated motel located 2 minutes from Catamount, 15 mins from Downtown Great Barrington & 20 mins from Hudson NY. Think cozy beds that give you the best ZZZs, Fast WiFi, & social media-worthy views that rack up the likes.brbrbrbrThe Space:brbrWe're dishing out some serious perks at our modern Hillsdale motel. Think top-notch amenities tailored for today's jet-setters. brbrbrbrGet Ready ForbrbrModern Digs: custom made everything, desk with built-in bench, headboard with USB outlets, painted concrete floors, refreshed bathroom, and newly designed vanity area with sleek mirror and small fridge. brbrbrbrBest ZZZs: One king size bed plus one queen pull out sofa both with high quality memory foam mattresses, two different size down alternative pillows, luxurious 100% cotton linens and custom made towels. brbrbrbrBrew Break & Beyond: Fuel up whenever you please with a handy in-room coffee pot, and gear up with a hair dryer and iron for looking sharp while on the go!brbrbrbrFast Wi-Fi: Stay connected without a hitch – perfect for sharing your vacay snapshots and staying in the loop.brbrbrbrBrookside Chill: The tranquil waters of the Roeliff Jansen Kill run through the 4 acre property. The river has a nice swimming and fishing hole and trout for catch and release!brbrbrbrPet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.brbrbrbrEasy Access: Park like a pro with our hassle-free parking, so you're all set to hit the road when adventure calls. One parking spot is included in your rental. brbrbrbrSupporting Local: Expertly designed and furnished by a local third generation textile maker, Tillett Textiles, including our hand printed wallpaper, vintage art and towels. brbrbrbrSave Dough $$: helping to keep your costs down by not having daily housekeeping & there’s no front desk. You’ll be able to check yourself in as you wish. Keep it simple, keep it savvy.brbrbrbrGuest Access:brbrNeed us A quick call or text, and we're on it!brbrbrbrOther Things to Note:brbrSave Dough $$: helping to keep your costs down by saving from not having daily housekeeping & there won’t be a front desk to check in you in but we’ll provide a door code you can check yourself in as you wish. Keep it simple, keep it savvy. brbrbrbrNeed us A quick call or text, and we're on it! brbrbrbrTraveling together Depending on what layout you reserved, our rooms can sleep 1 to 6 guests, have a larger group We also rent an onsite 5 bedroom house you may be able to reserve!

1

Bath

4

Sleeps

Exceptional(5)

$406.94

/ Nightly

Private Vacation Home

Lg Beautiful Country Home in Scenic Upstate NY!

Hillsdale, New York, United States

Large traditional country home with amazing scenery, nestled between the Berkshire and Catskill Mountains. 5 Bedrooms with plenty of additional living space to accommodate many guests. Lots of new furniture and beds. Linens and towels provided.brbrSecluded, but conveniently located:br• 5 minutes from Catamount Ski Area and the center of Hillsdale, NYbr• 15 minutes from Great Barrington, MAbr• 20 minutes from Hudson, NYbrbrOther amenities include:br• In-Ground Poolbr• 3x Living Rooms; main has brand new 60 smart TVbr• Large Dining Roombr• 2 Car Built-On Garage (electronic lifts)br• 2x Large Roofed-Patios (one on the house, one separate with a traditional brick BBQ grill and propane grill)

Bed

Bath

Sleeps

$897.49

/ Nightly

Private Vacation Home

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale, New York, United States

Welcome to your perfect summer getaway — a spacious, thoughtfully restored 7-bedroom farmhouse designed for connection, relaxation, and memory-making. With room for up to 14 guests (plus a crib), the home is ideal for family gatherings, group retreats, or a laid-back weekend escape with friends.brbrBEDROOMS & SLEEPING ARRANGEMENTS:brbrMain LevelbrBedroom 1: Queen bed + ensuite bathroom (window A/C)brBedroom 2: Queen bed (window A/C)brBedroom 3: Twin bed (window A/C)brBedroom 4: Twin bed (window A/C)brbrUpstairsbrBedroom 5: Two twin beds (window A/C)brBedroom 6: King bed + ensuite bathroom (floor A/C fans + portable window A/C)brBedroom 7: Two full beds + crib (window A/C)brbrBonus: One pack ’n play and one twin-size rollaway bed are also available.brbrAll bedrooms feature premium linens, cozy décor, and cooling units to keep guests comfortable through the summer months.brbrKITCHEN & DININGbrbr● Fully equipped chef’s kitchen with stainless steel appliancesbr● Keurig + drip coffee makers, wine fridge, spices, toddler plates & bowlsbr● Eat-in breakfast nook for 6br● Formal dining room with seating for 10—ideal for holiday meals and celebrationsbrbrGAME ROOM & ENTERTAINMENT:brbr● Game room with two arcade machines, poker table, and classic board gamesbr● Sunroom with indoor ping pong table, mountain views & 55” Smart TVbr● 5 Smart TVs throughout homebr● High-speed Wi-Fi for streaming or remote workbrbrOUTDOOR FEATURES:brbr● Private backyard with breathtaking hill viewsbr● Brand-new hot tub for crisp winter nightsbr● Two fire pits: propane lounge set + 10-person wood-burning pitbr● Weber grill, outdoor dining for 10, and string lights for cozy evening ambiancebrbrSeasonal PoolbrOur private pool is open from mid May through mid-October (weather permitting).brbr● Pool heating is available as an add-on amenity for $100 per day and applies to the full duration of the reservation..br● Please notify your host at least 48 hours before arrival if you’d like the pool heated so it’s ready for use at check-in.br● This fee covers the high energy cost required to maintain a comfortable temperature.br● Pool Heater Disclaimer:br While the Host will make every effort to keep the heater in good working condition, occasional malfunctions may occur. If the heater is unavailable, the daily fee will be fully refunded; no additional credits or refunds will be issued.brbrGeneral Amenitiesbr● Free Wi-Fibr● Radiator heating throughout the homebr● Hot tub towels, bed linens, and bath essentials providedbr● Toiletries (soap, shampoo, conditioner, body wash)br● Paper products and cleaning supplies includedbrbrWASHER/DRYERbrAn in-unit washer/dryer combo set. Complimentary scent-free detergent is provided for your stay.brbrPARKINGbr● Driveway fits up to 5 vehiclesbr● Parking permitted only in designated areasbr● Detailed parking info provided at check-inbrbrMAINTENANCEbrLawn care may occur during your stay.brWeekly hot tub maintenance ensures your comfort and safety.brbr***IMPORTANT NOTES***brbrSHORT-TERM RENTAL AGREEMENTbrAll guests are required to sign our Short-Term Rental Agreement upon booking.brIt includes important details such as check-in/check-out times, house rules, and stay guidelines.brbrPET FRIENDLYbrWe welcome dogs under 50 lbs (maximum of 2 dogs).br-Pet fee: $150 per pet, per staybr-No cats allowed at this time.br-Please let us know how many pets you’re bringing at the time of booking. Platform will automatically include the first pet fee.brFor additional pets, we’ll request an extra $150 per pet through the app. All pet fees must be paid prior to check-in.brbrPARTIES & GATHERINGSbrAbsolutely no parties or large gatherings allowed — no exceptions!brbrHILLSDALE TOWNSHIP NOISE ORDINANCEbrOur home is in a peaceful rural area, so please respect quiet hours.br-Quiet hours: 9 PM to 8 AMbr-No loud music should be played during these hours. Be mindful of our neighbors and the local ordinance.brbrSTAIRS REQUIREDbrThis charming historic farmhouse features a distinctive layout that enhances its character. Inside, you’ll encounter several small sets of steps, with the kitchen thoughtfully positioned on the opposite side of the living room. Two bedrooms are located on one side of the house on the second level, while a third bedroom is accessible via a separate staircase off the dining room. The home’s cozy, old-world charm is truly captivating, though the layout may be less suited for guests with mobility challenges.brbrFIREPLACE NOTICEbrThe indoor fireplace is currently not available for guest use.brbrSECURITY AWARENESSbr4 exterior security cameras are installed facing outward for guest and property safety. No cameras face any interior living spaces. Cameras do not actively record video or sound during guest stays.brbrWILDLIFE AWARENESSbrLocated in a rural area — you may spot deer, foxes, coyotes, or even bears. Please be cautious and avoid leaving food or trash outdoors.brbrTRAFFIC NOTICEbrOur home is along State Route 22, so you may hear outdoor traffic noise.brbrThank you and looking forward to your reservation!

Bed

Bath

Sleeps

$2184.0

/ Nightly

Private Vacation Home

3 bedroom house with a heated pool

Hillsdale, New York, United States

Indulge in ultimate luxury living in the heart of Columbia County, New York! This magnificent and spacious (6000 sq ft) house is a true gem that showcases breathtaking views of the stunning Berkshire Hills and majestic Catamount Mountains. Step inside and be greeted by double-height hallway leading to dining room with floor-to-ceiling windows, providing spectacular view of the pool area and stunning scenery beyond. Don’t miss this incredible opportunity to experience luxury living at its finest.brEnjoy dinner in the floor to ceiling windowed dining room or in the outdoor kitchen/dinning area. The formal Aramith dinning table, made in Belgium is one the world best fusion pool table with adjustable hights to make it a perfect dinning or playing experience.brThe gorgeous kitchen with its 12 foot island is well stocked with dishes, glassware, cutlery, cookware, two Mille ovens with the dish warmer, Mille dishwasher, Wolf professional grade 6 burners cooktop and a full coffee/tea setup. You'll have a wide variety of spices, oils, and other pantry goods. The kitchen opens to a spacious two-story Great Room with a warm and inviting fireplace and floor-to-ceiling windows that frame the stunning views. If you need a peaceful retreat, a cozy loft library is just a staircase away. Behind the Great Room, there is also an intimate home office space with a built-in closet, bookshelves, and bar, and can be used as an additional guest bedroom. Living room and formal dining room are equipped with high end, high fidelity audio equipment. There is large collection of vinyl records available for listeningbrThe first floor features two luxurious guest bedrooms, each with access to full baths and a gym with sauna and pool access, offering the ultimate relaxation experience. Each bedroom has an access door to outside allowing a full privacy to it’s guests. The upper level boasts a magnificent master suite with a double-sided fireplace, an oversized bathroom, and a private terrace. There is an oversize top-of-the-line Neptune whirlpool and adjustable mirror TV. There is easy access to a grand roof deck overlooking saltwater, heated pool, inviting hot tub, and outdoor kitchen. The grand deck has plenty of beautiful outdoor furniture which makes it perfect for entertaining!brThe lower level of this exceptional home is complete with a state-of-the-art movie room, a convenient laundry room, and a half-bath. Crip and play-yard for kids are available in the house. Situated on 32+ acres of beautifully landscaped property featuring expansive lawns and open country fields, this is the perfect country escape you’ve been searching for in Columbia County!

Bed

Bath

Sleeps

$1131.2

/ Nightly

Private Vacation Home

Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!

Hillsdale, New York, United States

This extremely private luxury home with Catamount Ski views and close to The Barn at Liberty Farms is situated on 33-acres at the end of a cul de sac and is located in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. This home has 5+ bedrooms (2 first floor masters) and 4 and 1/2 baths comfortably sleeps 14 plus people. With the bedrooms split so that the house feels private from all rooms. Eat-in-kitchen with a separate formal dining area. Cozy up with a book in the library with a w/fp. Other rooms include: living room, great room with wood burning stove, country office, 4.5 bathrooms, laundry room. The basement has full size pool table and ping pong, treadmill and spinner bicycle. The den includes a quality piano for your use. There is very large outside deck as well as a large screened in porch looking out at the Berkshire Mountains!. There is a beautiful swimming pond and a gazebo. Close to all major ski resorts (Catamount, Jiminy Peak and Butternut). Rail trails for biking. Many places to hike. Tanglewood, Jacobs Pillow, and more close. Trains to Manhattan nearby and available Uber as well.

Bed

Bath

Sleeps

$963.06

/ Nightly

Private Vacation Home

Wolf Hill Acres: A Charming & Modern Country Home

Hillsdale, New York, United States

Escape to Wolf Hill Acres! A private modern country retreat set on 20 private acres in the Hudson Valley.brbrWhether you're planning a group getaway, a family gathering, or a quiet escape, this spacious 5-bedroom home offers the perfect blend of comfort, nature, and entertainment.brbrIdeally located for relaxation and adventure: br• 15 minutes to Catamount Mountain Resortbr• 20 minutes to Hudsonbr• 25 minutes to Great BarringtonbrbrSpend your days exploring, and your evenings unwinding under the stars.brbrHave questions or need assistance We're just a message away. Enjoy a hassle-free stay with our instant communication.brbrDiscover the perfect blend of seclusion and convenience in Hillsdale, NY! brNestled in nature, our property offers tranquility, while being close to convenient stores and charming local shops. Embrace the best of both worlds.brbrEnjoy seamless, contactless check-in with your own personalized keypad code. No keys, no hassle.brbrA warm and inviting home designed for connection and comfort. brbrWith plenty of room to gather, or spread out, you’ll find everything you need for a memorable stay:brbr• Game room with pool table, foosball & ping pongbr• Smart TVs for movie nightsbr• Fully equipped kitchen for shared mealsbr• Cozy fireplace for relaxing eveningsbr• Board games for all agesbrbrThe outdoors:brWolf Hill Acres is more than just a home, it’s an experience. Wander our wooded trails, discover a cascading creek waterfall, or relax by the private pond.brbrEnjoy morning coffee on the front porch, then gather around the fire pit as the sun sets.brbrFeeling adventurous brTake the canoe out on the pond, go for a refreshing swim, or enjoy catch-and-release fishing.brbrCanoe Use at Your Own Risk: The canoe, related equipment and life vests are provided for your convenience and enjoyment. However, their use is entirely at your own risk. brNo Liability Assumed: The property owners assume no liability for any injuries, accidents, damages, or losses resulting from the use of the canoe, regardless of the circumstances.brbrA car is a must in Hillsdale, as ride shares are not available. Our three-car garage has room for large vehicles, and there's extra parking in the driveway.brbrFollow us @wolfhillacres for updates, special offers, and local tips.brbrWe’re proud to give back. Each booking supports the Hillsdale Blessing Box and helps our local community.

5

Bed

4

Bath

14

Sleeps

$549.61

/ Nightly

Private Vacation Home

Copake Lake Escape with Private Waterfront Access

Hillsdale, New York, United States

Summary:brbrRelax and unwind at this lakefront home on Copake Lake, featuring direct water access and beautiful views. This 2-bedroom retreat with loft and sleeper sofa sleeps 6 and offers a spacious kitchen, inviting living area, and private deck overlooking the water. Enjoy the fire pit, easy lake access, and a peaceful setting perfect for a memorable getaway.brbrbrbrThe Space:brbrSet along the shores of Copake Lake, this inviting lake house offers the perfect blend of comfort, space, and waterfront living. With direct lake access and peaceful views, it’s an ideal spot to relax, unwind, and enjoy one of Columbia County’s only motorized lakes.brbrbrbrThe home comfortably sleeps up to 6 guests across two bedrooms plus additional sleeping space. For easy planning, here are the sleeping arrangements:brbrbrbr Bedroom 1 (Main Floor): Queen Bedbrbr Loft (Upstairs): Queen Bedbrbr Common Area: Queen Sleeper SofabrbrbrbrThere is one full bathroom with a shower and features a heated toilet for added comfort.brbrbrbrThe spacious U-shaped kitchen is designed for gathering and cooking, with plenty of room for multiple chefs. It includes a gas range, peninsula seating for three, a dining table for four, and an in-sink dishwasher. Coffee lovers will appreciate the large 12-cup drip coffee maker and French press.brbrbrbrThe living area offers a relaxed setting with a stand-alone electric fireplace and a comfortable chair tucked into the corner, perfect for reading or taking in the lake views.brbrbrbrStep outside to fully enjoy the property. The deck overlooks the lake, creating a great space for morning coffee or evening drinks. A fire pit in the front yard adds to the experience, while a dedicated staircase leads down to your private lake frontage for easy access to the water.brbrbrbrWhether you're here for boating, relaxing by the fire, or simply enjoying the views, this lake house offers a memorable getaway in a beautiful setting.brbrbrbrOther things to get excited about:brbr-Mini Split air conditioning to keep you cool all summerbrbr-Laundry available for your convenience.brbr-Parking for two cars in front of the home and one behind the home.brbr-Approximately 8 stairs to the front doorbrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon!brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrbrbrDamage: Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

2

Bed

1

Bath

6

Sleeps

$871.93

/ Nightly

Private Vacation Home

Breezy Hill with Breathtaking Views!

Hillsdale, New York, United States

Breezy Hill, Hillsdale, NY: Light-filled 70′s contemporary with multi-level decks with outdoor seating, propane grill, screened porch, pond with dingy and floating dock, outdoor shower, and beautiful Catskill views. Just 1 mile from Ski Catamount with the awesome aerial ropes course adventure park in summer! Amenities include: 4 bedrooms, 2 full baths - Sleeps 8 in beds or 9 max, high speed internet, Smart TV with access to all subscription TV channels, AC throughout, wood burning stove, 7+ acres of hiking and cross country trails on the property, pack-n-play available (please bring our own baby sheets) All house linens are included. House is 2600 Sq Ft and available for all seasons. brbrBreezy Hill has beautiful views of the Catskill Mountains, wrap-around decks, a screened porch, wood stove, and pond and more, just 1 mile from Ski Catamount. Guests come in through the front door and up a staircase to access the main living space. Once upstairs, the kitchen, dining room and living room are open concept and well situated, with a wall of glass sliders. This top level deck wraps around the living room and dining room and includes Adirondack chairs, table with umbrella, and a gas grill. The furnished screened porch is right off the kitchen and allows for outdoor enjoyment and dining al fresco. The kitchen has stainless appliances, storage and counter space, and plenty of cooking gadgets. This upper level also has the ensuite primary bedroom with a Queen bed and full bathroom with tub/shower combination. brbrThe lower/main floor has 3 bedrooms: Guest room #2 has a King bed, Guest room #3 has a Queen bed plus a small fold out futon bed, and Guest room #4 has 2 twin beds. These 3 guest rooms all share a newly redone full bathroom with a shower. There is also an outdoor shower with hot/cold running water, available seasonally. The media room is also on this main floor and has a Smart TV with access to your subscription TV channels! This room also has sliding doors that lead to the lower deck - also with outdoor seating. The washer and dryer are located in the basement and the access to the outdoor shower is either through the basement or from the back yard. There is a Pack N Play available (guest brings their own sheets). brbrOutside, features include a pond with a floating dock, a small creek running along the edge of the property, and 7+ acres of land to explore and hike. Please note, Fishing in the pond is catch and release only In winter, just step out the front door for great sledding, snowshoeing or skating on the pond - only when weather conditions permit.brbrThe house is perfectly located - less than 30 minutes to Hudson for great food, art galleries and antiquing. 15 minutes to Great Barrington for food, shops and restaurants. For hikers, Bash Bish Falls is a 10 minute drive as is the Appalachian Trail.brbrFor skiers you are only one mile from Catamount or 20 minutes to Butternut. Summer renters can enjoy this remote location but still be within a short drive to all the cultural events the Berkshires are known for. brbrBreezy Hill is pet friendly, however, pets must be approved and, typically, a $150 minimum pet fee applies. (Cats are not permitted due to allergies.)brNon Smoking, Thank you!

Bed

Bath

Sleeps

$352.8

/ Nightly

Private Vacation Home

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Hillsdale, New York, United States

Post and beam country home with lake rights on beautiful Copake Lake only 2 hrs from NYC. Perfect for Summer activities, a Fall weekend or Winter skiing at nearby Catamount. (Ski Season Rental also available.) Enjoy this charming home with large sliding glass doors and windows surrounding the open dining, living and kitchen areas. Large two-tiered deck overlooks the lawn and forested property with grill, picnic tables and lounge chairs. The main living area, which is one flight up, has two cozy bedrooms, each with double bed and closet and one full bathroom with shower/tub. Additionally, there is a master loft bedroom with queen bed, closets, bathroom, plus separate reading nook. One pull out queen couch on main floor living room provides extra sleeping. Copake Lake is a 5 minute walk (or you may drive) down a private gravel road to a shared area that provides access to swimming and picnic table. Kayak and boat rentals available at Marina. A short drive to grocery stores, farm markets, hiking trails, restaurants and gas stations. Nearby Copake Country Club offers golf and indoor/outdoor dining. Hudson, Great Barrington and other Berkshire and Catskill activities close by. This home has central air conditioning and is fully winterized with wood stove and electric baseboard heat. An ideal location, in any season, for your perfect getaway in the country!

Bed

Bath

Sleeps

$273.65

/ Nightly

Private Vacation Home

It's All About the Mountain Views, Modern Farmhouse

Hillsdale, New York, United States

Separate private entrance of main house to a large, En Suite apartment in fully built out bottom floor. One bedroom with very comfy queen size bed, streaming tv, huge comfy couch. Private bathroom with shower, toiletries and blow dryer. Main living area has an additional queen sized pull out sofa. Enjoy coffee on the outdoor patio overlooking the Hudson Valley Mountains. Hiking trail on property, minutes from The Berkshires, Hudson, restaurants, culture and nature.

Bed

Bath

Sleeps

$448.0

/ Nightly

Country House

Farm House Getaway on beautiful horse farm!

Hillsdale, New York, United States

No pets allowed. Escape the hustle and bustle of daily life, and find yourself transformed in a place of total relaxation and peacefulness. Delight in the bird song, fresh air and expansive views! Curl up on the front porch with a glass of wine, or sink into the over-sized couch with a favorite book. The cozy bedrooms are all appointed with fine cotton linens and down pillows, and the bathrooms are stocked with quality towels. The large kitchen will encourage your creative 'inner' chef, with commercial appliances and a full array of cooking and bake ware. The dining room accommodate a hungry crowd of 8 to 10 comfortably. brbrThe Farm House is conveniently located just over 2 hours from both New York City and Boston, with easy access by Amtrak and Metro North trains. Situated on 60 hillside acres, you will feel miles from civilization, but when the mood strikes, find yourself just 20 minutes to high-end restaurants and shopping in either Hudson, NY or Great Barrington, MA. A wealth of nearby cultural attractions include Tanglewood, Jacob's Pillow, Berkshire Choral and Theater Festivals, as well as Golf, Catamount's Adventure Park, the Rail-Trail, plus art house movies, and miles of hiking trails, waterfalls and swimming holes ...Skiers will feel right at home near 3 major ski resorts, Catamount, Jiminy Peak and Butternut!brbrTastefully decorated, this renovated Colonial sits apart, on what was once New England's most renowned Arabian horse farms, now being revitalized, lacking nothing in the natural beauty of it's charming landscape and stunning views! Horses roam the lush green pastures, adding to the enchantment of this country destination. Replete with all the necessary amenities, perfect for a family or a small group of discerning adults, we are excited to welcome you to our Farm House - your home-away-from-home, in a beautifully tranquil location, sure to create wonderful memories! Note: Base fee is for 4 guests only, additional guests are billed at $55/person/night up to 10 max

4

Bed

2

Bath

10

Sleeps

$252.0

/ Nightly

Chalet

Beautifully decorated & immaculate log chalet on 3 acres, winter views.

Hillsdale, New York, United States

Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet has gorgeous stone countertops in the kitchen. Our home is beautifully decorated and immaculately clean because we take pride in knowing that all our guests will be happy and remember their stay with us. We are located under one mile from Catamount ski area and 20 minutes to Butternut ski area. Biking, fishing, swimming, hiking and horseback riding, golfing and antique auctions are just some of the many activities in the area. Close to several attractions such as Norman Rockwell Museum and Red Lion Inn in Stockbridge, MA, Shaker Museums and many superb restaurants. Bish Bash Falls is minutes away and Great Barrington, MA is within ten minutes for great window shopping. See the breathtaking views from the top of Mt. Washington. brbrbrScenic Surroundings and Nearby Attractions: This br property is conveniently located between routes 22 and 23 in Hillsdale, New York, within one mile of Catamount ski area in NY and within 20 minutes of Butternut ski area in MA. The property is an easy two hour drive from New York City. Great Barrington, Massachusetts, with all its trendy shops and restaurants is only ten minutes away, and Stockbridge, Massachusetts is only a 30 minute drive away; there you can explore Norman Rockwell paintings and various other museums and attractions. Lenox, MA and the shopping outlets in Lee, MA are also 30 minutes away. Jimeny Peak ski area is a 35 minute drive. Take a scenic drive down the Mohawk Trail and visit the shops while taking in breathtaking views of the mountain region, or just take a relaxing walk through the woods and explore the beautiful fall foliage. Bring your skis and cocoa and enjoy the beautiful views of the season.

3

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Hillsdale, NY

$356.76

$490.5

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$2184.0

$1131.2

$963.06

$549.61

$871.93

$352.8

$273.65

$448.0

$252.0

Most popular vacation rentals in Hillsdale

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