Vacation Rentals By Owner In Hillsdale, NY

$415.8

Meadowland Farmhouse with Beautiful Sunsets n5 minutes from town

Hillsdale, New York, United States

Our cozy home is located in the heart of the Berkshires, midway between NYC and Boston. This newly renovated modern rustic-style home sits on three acres just five minutes from the town of Hillsdale, 20 minutes from the town of Great Barrington and 20 minutes from the town of Chatham. In the summer you're near Taconic State Park, Tanglewood, multiple performing arts venues, theaters, museums and plenty of hiking trails.brbrIn the Fall enjoy apple and pumpkin picking, and watch the leaves turn beautiful colors. In the winter you can enjoy multiple ski slopes nearby and, plenty of winter activities. In the spring, watch as nature wakes up from the winter months. Our area is a paradise for bird watchers, writers and artists. (You can take classes at the Art School in Ghent NY). If you're an amateur chef, take a cooking class at HGS Home Chef in the town of Hillsdale. brbrOr just enjoy the grand spectacle of a beautiful sunset from our wraparound porch.brbrTHE SPACEbrbrOur house has something for the whole family to enjoy, and there's plenty of room for everyone, and we are fully accessible, with a wheelchair ramp and wide doorways.brbrOn the first floor is an en-suite master bedroom with floor-to-ceiling windows. A large living room with a propane gas fireplace and a 52-inch television for those winter or rainy nights; a large kitchen with brand-new appliances, all the cooking utensils you'll need; a dining room that sits six to eight; and the kitchen island accommodates four more.brbrOnce outside, you'll find a front porch that wraps around the side of the house, with four rocking chairs and a porch swing for lazy afternoons. There's another porch in the back with a picnic table and BBQ grill where you can watch the sunsets over the nearby farm.brbrOutside the first-floor master en-suite bedroom there is another porch where you can enjoy your morning coffee. We have a fire-pit with Adirondack chairs for chilly nights, where you can sit around and tell stories, drink hot chocolate and roast marshmallows. We provide plenty of cozy blankets.brbrSECOND FLOOR brbrOn the second floor, there is another master bedroom with a queen-size bed, a second room with double twin beds (which can be combined to make a king-size bed with the help of a mattress topper); a small library/office alcove, with a daybed (with an additional trundle bed), and a full bathroom with double sink and a soaking tub.brbrTHIRD FLOORbrbrOn the third floor, we have a kids-only attic with a chalkboard and an arcade machine featuring classic games like Pac-Man and more. We have a futon which converts into a full-size bed. A television and DVD player will help keep the children entertained.brbrLOCATIONbrbrOur convenient location offers easy access to all that the beautiful Berkshires, Western Massachusetts and the Hudson Valley have to offer year-round.brbrLocated just minutes away from lots of great places. There are so many things to do in our extended neighborhood. Great restaurants, breweries, bars, performing-arts centers, museums & galleries, antiquing, winter sports, water sports, hiking, farms, horseback riding, cideries, wineries and amazing vineyards to visit. Please always feel free to inquire for more information regarding these activities.brbrSome of the nearby neighborhoods to visit are only minutes away; Great Barrington; Egremont; Copake; Chatham; Ghent; Lee; West Stockbridge; Hudson; and so many more.brbrThis property is family owned and operated. We are always available to answer your questions before and during your stay.

5

Bed

2

Bath

8

Sleeps

$213.84

/ Nightly

Agritourism

Private Unit in shared 1830 Farmhouse

Hillsdale, New York, United States

Welcome to The Johnson Farmhouse, a delightful retreat steeped in charm and history, located in the heart of the picturesque hamlet of Hillsdale, NY. brbrLocation, Location, Location!brbrNestled just minutes away from an array of restaurants, shops, and grocery stores, you’ll find everything you need right at your fingertips. For outdoor enthusiasts, Catamount Mountain Resort is only 3.2 miles away, offering skiing in the winter and an exhilarating aerial park in the summer. A short 15-minute drive east will take you to the stunning Great Barrington, MA, while a 16.9-mile drive west leads you to the trendy upstate gem of Hudson, NY. Don’t miss exploring charming nearby towns like Millerton and Chatham, each offering its unique character and attractions.brbrCultural and Outdoor ActivitiesbrbrThe Johnson Farmhouse is perfectly situated for those looking to immerse themselves in the rich cultural and outdoor activities of the Hudson Valley and Berkshires. Discover the breathtaking Bash Bish Falls, enjoy a performance at Tanglewood, experience the art of dance at Jacob's Pillow, or explore the stunning installations at Art Omi. Plus, for cycling enthusiasts, the scenic Harlem Valley Rail Trail is less than a mile away—perfect for a leisurely ride through beautiful landscapes!brbrThe SpacebrbrYou’ll have private access to half of the farmhouse, including a charming main entry and foyer, a spacious living room that doubles as a dining/game room, a sun-soaked sun porch, and a screened-in porch perfect for relaxing with a book. Choose between a restful King bedroom and a charming Queen bedroom, both designed for comfort, and enjoy the convenience of a private bath.brbrWhile this rental does not include a full kitchen, we’ve equipped a kitchenette with a microwave, Keurig coffee maker, and apartment-sized refrigerator for your convenience. Enjoy complimentary coffee pods, sugar, and eco-friendly disposable plates, flatware and coffee cups (with lids) during your stay.brbrExperience the perfect blend of historic charm and modern comfort at The Johnson Farmhouse; the perfect base to exploring the natural beauty and cultural richness of the Hudson Valley and Berkshires.

2

Bed

1

Bath

4

Sleeps

$1310.97

/ Nightly

Private Vacation Home

Newly renovated private 3 bedroom house on a dead end road.13 acres & 360 views

Hillsdale, New York, United States

Welcome to your dream upstate country escape! This newly remodeled 3-bedroom, 3-bathroom home offers a perfect blend of modern luxury and natural beauty. Nestled at the end of a dead-end road on 13 acres, this stylishly designed residence provides ultimate privacy and tranquility. We look forward to hosting you at our place.

Bed

Bath

Sleeps

$1127.83

/ Nightly

Private Vacation Home

Chef’s Kitchen, Fast Wi-Fi

Hillsdale, New York, United States

We are on 35 acres, on top of a mountain and the views of the Hudson Valley mountains are spectacular. Enjoy your first cup of coffee in the morning or a glass of wine in the evening overlooking outstanding mountainous views. I promise, you will not be disappointed. You will have access to Chef’s kitchen, fast wireless internet, free parking, hiking trails, swimming pond and kayaks, custom fire pit with grilling capabilities, Big Green Egg,

6

Bed

4

Bath

14

Sleeps

$853.83

/ Nightly

Private Vacation Home

Wander Hillsdale Lakeside

Hillsdale, New York, United States

Welcome to Wander Hillsdale Lakeside, a stunning lakefront home featuring modern architecture and captivating sunset views. This elegant residence includes top-tier amenities like a gym, a cozy fireplace and an office. With its blend of contemporary design and serene lakeside living, Wander Hillsdale Lakeside offers an ideal retreat for both comfort and beauty.

3

Bed

4

Bath

6

Sleeps

$10426.63

/ Nightly

Private Vacation Home

The Brooks Buy Out, Wedding Groups Inquire Today!

Hillsdale, New York, United States

Summary:brHosting an event at Catamount or Taconic Ridge Farms Direct your guests to The Brooks Motel, located directly across from Taconic and only 3 mins to Catamount. Ideal for any group size up to 60. brbrNote: Prices seen are for estimation. For accurate rates, please reach out!brbrThe Space:brWe're dishing out some serious perks at our modern Hillsdale motel. Think top-notch amenities tailored for today's jet-setters. brbrGet Ready ForbrModern 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. brbrBrew 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!brbrFast Wi-Fi: Stay connected without a hitch – perfect for sharing your vacay snapshots and staying in the loop.brbrBrookside 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!brbrPet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.brbrEasy 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. brbrSupporting Local: Expertly designed and furnished by a local third generation textile maker, Tillett Textiles, including our hand printed wallpaper, vintage art and towels. brbrSave 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.brbrOther Things to Note:brReach out for a custom quote, pricing for estimation purposes only!

Bed

Bath

Sleeps

$446.04

/ Nightly

Private Vacation Home

Secluded Country Getaway On 22 Magical Acres. Catamount ski resort 5 min away

Hillsdale, New York, United States

The adventure awaits in the Berkshires. Escape the hustle and bustle of your everyday life and come chill in a renovated grist mill on 22 acres. This getaway is located .5 miles from Catamount and 4 to Butternut. The property has a 10 Ft pound, waterfall and a babbling brook that can be viewed from every window. Enjoy the lush views and walking trails on the property. There are 4 fire pits on the property. I try to keep logs by the fire pit but if there has been rain and it is wet, Stewart’s sells packs of wood in an easy to carry pack. I have fire starters, long lighters and the colorful burn sticks.brYou can choose the Hudson food and art scene or the Great Barrington/Egremont Massachusetts food, antique shopping and hiking scene. Tanglewood is only 14 miles away. The home is decorated with Piet Boon furniture and other unique pieces. There is a full kitchen for your own culinary experience or you can call our chef and order off her ever changing menu. She can cook breakfast, lunch or dinner and deliver to the home at whatever time you request. Prices are reasonable. There is a delivery charge. I have a groundskeeper that lives nearby that is available 24 hours a day for your convenience. brbr******PLEASE READ HOUSE RULES CAREFULLY *******

Bed

Bath

Sleeps

$354.09

/ Nightly

Private Vacation Home

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale, New York, United States

Summary:brWelcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 5 comfy bedrooms, 2 full baths, a proper dining room with gas fireplace, & tons of space for your group inside and out. Set on 2 acres enjoy the large grassy and private river access.brbrOnly two mins from Catamount Ski Mountain and close to Downtown Great Barrington & Hudson, NYbrbrThe Space:brWelcome to your affordable home away from home, perfect for making the most of all that the Hudson Valley and Berkshires has to offer - whether you're unwinding or seeking adventure through hiking, skiing, antiquing, and enjoying local cuisine.brbrAs you step inside, a warm entryway welcomes you. To the left, you'll discover the inviting living room, while to the right, you'll find the dining room, sunroom, and fully-equipped kitchen.brbrThe living room boasts a generous 54-inch smart TV equipped for streaming. Feel free to use your own Netflix and other streaming services.brbrThe dining room is designed for entertaining with it’s gas fireplace, boasting an extra-long table with seating for eight, and a china cabinet stocked with plenty of dishes and glassware to host a killer dinner. Adjacent to the dining room, you'll find a bright sunroom, offering additional lounge seating.brbrThe kitchen features a dining table accommodating six, stainless steel appliances (refrigerator, gas stove, microwave, and dishwasher), and it's well-equipped with all your cooking and serving essentials, including cookware, pots, pans, plates, cups, and silverware.brbrAll five bedrooms are located on the second floor of the house. One bedroom boasts two queen beds, while the other four bedrooms each feature one queen bed. The upstairs master bedroom includes a separate office space, ideal for those who need to work remotely.brbrThere are two bathrooms on the second floor - one with a tub/shower combo and the other with a stand-up shower.brbrAnd there's more to look forward to:br-High-quality memory foam mattresses and hotel-grade 100% cotton linens and towels.br-Hardwood floors in the living room and dining room, tiled kitchen, and painted wood floors throughout the rest of the house.br-Window AC units to keep you cool in summer and radiator heating to keep you cozy in winter. Gas fireplace in the dining room.br-Please note that there are around 12 stairs leading to the bedroom and bathroom area, so it may not be ideal for guests with limited mobility.br-Parking is limited to three cars.br- Pet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.br-There is a laundry room off the house that is used by the housekeeping for the motel, they will not access the house at all while you are staying. Additionally there is an in law suite that we rent seperatly, if you wish to rent house as a 6 bedroom 3 bathroom including the in law suite, please let us know! brbrWe invite you to relax, unwind, and make cherished memories in this welcoming home - your gateway to the best of the Hudson Valley!

5

Bed

2

Bath

12

Sleeps

$215.88

/ Nightly

Cottage

Underhill Cottage

Hillsdale, New York, United States

About this spacebrCharming 1948 light filled cottage, recently gut renovated. It has two, cozy, queen guest bedrooms and a twin daybed. There are two, new, full bathrooms with vintage details. The wood burning fireplace adds that perfect touch for your country getaway.brThe spacebrIn addition to the living room, there’s a south facing sun room where you can have coffee, and a large rev room in the basement to watch tv, put together a jigsaw puzzle or work at your laptop.brGuest accessbrGuests have access to the entire house.

Bed

Bath

Sleeps

$184.86

/ Nightly

Private Vacation Home

Country Karma -Quiet Wooded Getaway

Hillsdale, New York, United States

You're considering renting a modern saltbox house, perched on a hilly wooded property, overlooking pristine Columbia County Conservancy land. Meals cooked on the Viking stove or on the Weber taste better. On summer nights you may be lulled to sleep by the sound of frogs in the nearby creek.brbr- 2 hours from NYC br- From the house: if you're inclined toward outdoor sports, there is no shortage of great routes for running, road and off-road cycling, and of course long walks. br- Nearby destinations: swimming in Guilder Pond, Catamount, Hudson Valley Rail Trail, Lake Taghkanic State Park, kayaking in Copake Lake, swimming and fitness center at Taconic Hills School br- Short drive to Hudson (NY): antique shopping, restaurants, music at Helsinki, movie theaters, Time Space Limited, Amtrak, many chain stores br- Short drive to Great Barrington (MA): restaurants, Guido's Fresh Market, Big Y, shopping, movies br- Easy drives to Berkshire destinations: Tanglewood, Jacob's Pillow, Mass MOCA, the Norman Rockwell Museum, The Clark, Shakespeare and Co., the outlets in Leebrbr2 bedrooms with full-size beds and connected bathbr1 bedroom with queen-size bed and adjacent bathbr1 bedroom with 2 twin bedsbrbrExcept for the basement, guests have access to the whole house. Long term guests pay for services such as electricity, gas, cleaning, yardwork, telephone and internet.

4

Bed

3

Bath

10

Sleeps

Select Dates for Price

Private Vacation Home

R&R in the treetops with lrg outdoor living space and all the comforts of home.

Hillsdale, New York, United States

Need to get away from the city for some rest and relaxation but stay connected Stay in our rural, quiet getaway. Huge outdoor space with grill, dining table (seats 8), cafe table, lounge chairs, hammock, jacuzzi, outdoor shower and if you need more than that, you're so close to Hudson, NY and Great Barrington, MA with incredible dining, theatre, music, dance performance, skiing, swimming, golfing, museums... Just what the doctor ordered for those jangled nerves.

Bed

Bath

Sleeps

$419.13

/ Nightly

Private Vacation Home

Apple Blossom Cottage by Evergreen Home

Hillsdale, New York, United States

6 MINUTES FROM CATAMOUNT MOUNTAIN brbrA newly renovated, thoughtfully designed mid-century retreat featuring a gourmet kitchen, high-end décor, 4K home theater, log fireplace, and luxurious bedding. Enjoy upscale bathrooms with complimentary toiletries and plush spa-like robes. Unwind by the fire pit or savor homemade pizza with the Ooni oven under the starry sky. Complete with a new washer/dryer and ultra-fast Wi-Fi, this gem is ideally located near farm markets, cideries, and ski mountains.brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThe home is rural, located off the main road. brbrGuests will have private access to the entire home, and property.brbrThe gourmet kitchen is fully equipped with everything you need to cook up that special dinner including top of the range appliances, a family sized food processor, microwave and blender. A breakfast bar provides extra seating in addition to the formal dining table. brbrThe cozy living room creates the perfect atmosphere for days at home. A state of the art projector with 4K image and theater sound brings the big screen to the living room. Ultra-fast Wi-Fi is perfect for streaming (enjoy complimentary Hulu + Live TV, Netflix and Disney+). Use the popcorn maker to complete the movie night vibe! Or just snuggle up under a blanket next to the roaring fire with a book or game.brbrLuxury mattresses, plush duvets and Brooklinen bedding bring blissful comfort to the bedrooms so that you are fully refreshed. The stylish primary bedroom features a platform king bed, desk, and newly remodeled ensuite bathroom. The second bedroom contains a queen sized bed. The second full bathroom is close by and is newly remodeled with elegant subway tile. Eco-friendly toiletries, organic towels, fluffy robes and slippers create that spa experience to rejuvenate at the end of the day.brbrTake advantage of the oversized desk in the second cozy living room or den, surrounded by greenery, to create your ideal work from home space. The den also houses an additional full sized bed for another sleeping option.brbrStep out and enjoy nature! All around are views of trees and rolling hills, and you may be joined by the occasional deer as you enjoy your morning coffee on the patio. Find a perfect place to enjoy outdoor cooking with the charcoal grill and wood-fired pizza oven, and as the night rolls in, share stories around the firepit under the stars.brbrThe double garage is well stocked with firewood and offers storage for your bikes, skis, boards, and boots. A new washer and dryer in the basement is available.brbrThe desirable location of this home makes for easy access to Hillsdale-farm markets, cideries, and state parks.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively. Easy access to the Taconic Parkway, 4WD is suggested in the winter season.brbrLOCATION: The home is rural, located off the main road. brPETS: No pets.brPARKING: Free parking on premises.brbr**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

Bed

Bath

Sleeps

$784.5

/ Nightly

Private Vacation Home

Waterfalls and Trails at 'The Mills At Green Hole'

Hillsdale, New York, United States

Travel back in time to a secluded and beautiful place known as 'The Mills at Green Hole,' a historic 6-bedroom, 3-bathroom house complete with a water-powered mill, swimming holes, hiking trails, and more. Outdoorsy families seeking a unique experience near the Berkshires will enjoy everything this vacation rental has to offer including a fully equipped kitchen, sunroom, an extensive library, farmhouse, a large yard, and 2 floors of country living space. Quality R&R awaits you and your family!brbr-- THE PROPERTY --brbr3,600 Sq Ft | On-Site Stream & 2 Waterfalls | Charcoal & Gas Grills | 30 AcresbrbrJust a short drive from Catamount Mountain Resort, New Forge State Forest, and a variety of orchards and farms, this pleasant home allows you to have a worry-free stay in a serene natural setting.brbrBedroom 1: Full Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed | Bedroom 4: Full Bed | Bedroom 5: Full Bed | Bedroom 6: Twin Bunk Bed, Twin Bed | Living Room: Sleeper SofabrbrOUTDOOR LIVING: Yard, fire pit, hammock, on-site stream & swimming holes, water-powered mill, hiking trailsbrINDOOR LIVING: Smart TV, iPod/MP3 dock, DVD player, movie collection, board games, extensive library, fireplace (decoration only), wood-burning stove, en-suite bathroom, laptop friendly, piano, dining tablebrKITCHEN: Fully equipped, coffee maker, coffee grinder, hot water pot, microwave, pots & pans, cooking utensils, Crock-Pot, blender, toaster, toaster oven, spices, wood-burning oven (decorative only), dishware & flatware, breakfast bar brGENERAL: Free WiFi, central heat, window A/C, beach towels, towels/linens, washer/dryer, hair dryerbrFAQ: Pet fee (paid pre-trip), no fence around stream, stairs required for entry & 2nd-floor bedroom access, 1 exterior security camera (facing front porch)brPARKING: Partially-blind driveway (4 vehicles), additional parking (10 vehicles), RV/trailer parkingbrbr-- THE LOCATION --brbrOUTDOOR FUN: High Falls Conservation Area (3.0 miles), Harrier Hill Park (10.8 miles), Promenade Hill Park (12.2 miles), Greenport Conservation Area (12.6 miles), New Forge State Forest (13.9 miles), Bash Bish Falls (15.4 miles), Athens Riverfront Park (22.7 miles), Four Mile Point Preserve (27.2 miles), Falling Waters Preserve (34.4 miles)brSKI SLOPES: Catamount Mountain Resort (10.0 miles), Butternut Ski & Tubing Area (22.4 miles), Mountain Trails Cross Country (36.3 miles), Hunter Mountain Resort (40.2 miles)brPARS + BIRDIES: Copake Country Club (7.2 miles), New York Golf Park (10.1 miles), Catskill Golf Resort (21.1 miles), Thunderhart Golf Course (32.5 miles)brORCHARDS + FARMS: Hawk Dance Farm (6.5 miles), L H Farms (6.9 miles), Philip Orchards (7.4 miles), Little Apple Cidery (9.7 miles), Markristo Farm (9.9 miles), Taconic Orchards (12.2 miles), Copake Valley Farms LLC (13.3 miles), Vosburgh Orchards (18.4 miles)brATTRACTIONS: FASNY Museum of Firefighting (11.8 miles), Hudson Athens Lighthouse (13.1 miles), Rip Van Winkle Bridge (17.9 miles), Thomas Cole National Historic Site (18.8 miles), Olana State Historic Site (18.9 miles), Five State Lookout (35.7 miles), Amtrak Albany NY (40.4 miles)brAIRPORT: Albany International Airport (49.1 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 per stay fee (+ taxes & fees)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires stairs to enter & to access the 2nd-floor bedrooms. These areas may be difficult for guests with limited mobilitybr- NOTE: The wood-burning oven and the fireplace are for decoration only and are not available for guest usebr- NOTE: This property may not be suitable for small children due to no fence along the on-site stream. Adult supervision is required at all timesbr- NOTE: Your safety matters. This property features 1 exterior security camera located on the front porch, facing outward. It does not look into any interior living spaces. The camera does not actively record video or sound while guests are in residence

Bed

Bath

Sleeps

$359.85

/ Nightly

Private Vacation Home

Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

Hillsdale, New York, United States

Summary:brWelcome to this beautiful historical house! We've given this budget-friendly, vintage gem a refresher with 6 comfy bedrooms, 3 full baths, a proper dining room with gas fireplace, & tons of space for your group inside and out. Includes 5 bedroom guest house plus attached in law suite! brbrOnly two mins from Catamount Ski Mountain and close to Downtown Great Barrington & Hudson, NYbrbrThe Space:brWelcome to your affordable home away from home, perfect for making the most of all that the Hudson Valley and Berkshires has to offer - whether you're unwinding or seeking adventure through hiking, skiing, antiquing, and enjoying local cuisine.brbrAs you step inside, a warm entryway welcomes you. To the left, you'll discover the inviting living room, while to the right, you'll find the dining room, sunroom, and fully-equipped kitchen.brbrThe living room boasts a generous 54-inch smart TV equipped for streaming. Feel free to use your own Netflix and other streaming services.brbrThe dining room is designed for entertaining with it’s gas fireplace, boasting an extra-long table with seating for eight, and a china cabinet stocked with plenty of dishes and glassware to host a killer dinner. Adjacent to the dining room, you'll find a bright sunroom, offering additional lounge seating.brbrThe kitchen features a dining table accommodating six, stainless steel appliances (refrigerator, gas stove, microwave, and dishwasher), and it's well-equipped with all your cooking and serving essentials, including cookware, pots, pans, plates, cups, and silverware.brbrAll five bedrooms are located on the second floor of the house. One bedroom boasts two queen beds, while the other four bedrooms each feature one queen bed. The upstairs master bedroom includes a separate office space, ideal for those who need to work remotely.brbrThere are two bathrooms on the second floor - one with a tub/shower combo and the other with a stand-up shower.brbrThe house also comes with an inlaw suite which includes a queen size bed, a 2nd full size kitchen, and bathroom with stand up shower. brbrAnd there's more to look forward to:br-High-quality memory foam mattresses and hotel-grade 100% cotton linens and towels.br-Hardwood floors in the living room and dining room, tiled kitchen, and painted wood floors throughout the rest of the house.br-Window AC units to keep you cool in summer and radiator heating to keep you cozy in winter. Gas fireplace in the dining room.br-Please note that there are around 12 stairs leading to the bedroom and bathroom area, so it may not be ideal for guests with limited mobility.br-Parking is limited to four cars.br- Pet-Friendly Vibes: Furry friends welcome! Bring your buddy along for the journey, no extra fees.br-There is a laundry room off the house that is used by the housekeeping for the motel, they will not access the house at all while you are staying! brbrWe invite you to relax, unwind, and make cherished memories in this welcoming home - your gateway to the best of the Hudson Valley!

Bed

Bath

Sleeps

$389.9

/ Nightly

Private Vacation Home

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hillsdale, New York, United States

Escape to Serenity in the Heart of the Berkshires: A Modern Retreat Surrounded by NaturebrbrImmerse yourself in the awe-inspiring tranquility of the Berkshires within this secluded and contemporary home, offering breathtaking mountain and rolling meadow views on 6 acres of stunning countryside. Tucked away at the end of a winding country road, this haven ensures complete privacy, providing the perfect sanctuary from a hectic schedule.brbrOnly a 9-minute drive from the Taconic Parkways and strategically located near Catamount Ski, Butternut Ski, and Copake Lake, this residence seamlessly combines country living with modern convenience. A scenic 50-minute drive takes you to Jiminy Peak Mountain Resort Ski and Bousquet Mountain Ski Area for a winter wonderland retreat.brbrThis beautiful home, boasting an open floor plan, features 4 bedrooms, 2.5 baths, an inviting kitchen, and multiple spacious living areas, including a wood-burning fireplace. Revel in al Fresco dining on the deck, overlooking mountain vistas, or cozy up by the fireplace for intimate moments with loved ones.brbrThe upper level hosts 4 bedrooms, including two master suites with luxurious amenities. The main level's expansive living space opens to a deck with multiple seating areas, perfect for gatherings. Downstairs, discover a recreation haven with a ping pong table, a Smart TV lounge, and sliding doors leading to an outdoor deck.brbrEnjoy high-speed fiber optic internet, ensuring seamless remote work or streaming, facilitated by premium WiFi systems. Fully furnished and strategically located 100 miles from NYC and 150 miles from Boston, this rustic yet modern retreat awaits your year-round escape. Keywords: Bash Bish Falls, Catskills, Summer, Weekend, Hudson Valley, Skiing, Hiking, Tanglewood, Winery, Stargazing.

4

Bed

3

Bath

8

Sleeps

$369.9

/ 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.

3

Bed

2

Bath

7

Sleeps

$472.36

/ Nightly

Private Vacation Home

Mountain View: Airy + Secluded w/Panoramic Views

Hillsdale, New York, United States

Summary:brWelcome to Mountain View, a beautifully appointed 3-bed, 2.5-bath home perched on the mountainside—just 2.5 hrs from NYC. brbrSprawling mountain views set the stage for this inviting home. High ceilings and large windows fill the home with nautral light and mountain views. The open-plan design reveals a living area with a fireplace, a modern kitchen and dining area. Enjoy an elevated deck and screened-in porch; and a TV room downstairs.brbrNearby towns: Hillsdale (12 min), Great Barrington (25 min)brbrThe Space:brAs you round the bend of the driveway, you’ll catch your first glimpse of the sprawling view, and lush foliage lines the walkway to the front door. Entering into the bright, open interior is like a deep breath that immediately lifts the spirits. High ceilings and expansive windows bring in the glow of natural light even on grey days. Gorgeous mountain views greet you once again from the entry, and nearly every room throughout the house.brbrA tidy half bath is conveniently located just off the front door, with the open kitchen/living/dining spaces unfolding to your right. This is the perfect space for gathering and catching up before, during, and after a meal, or a lovely spot for quiet contemplation while admiring the view. A large sectional sofa anchors a seating area that invites relaxation and coziness (complete with a wood stove for the colder months). Cooks will rejoice at the sight of the well-appointed kitchen’s thoughtful layout and ample counter space. The kitchen and generous dining table beyond are sure to inspire memorable meals shared against the panoramic backdrop of meadows and mountains.brbrIn warmer months, a back deck hosts beautiful potted plants, comfy chairs - a perfect spot to enjoy your morning coffee or a late afternoon cocktail. The screened porch offers a delightful spot to enjoy an alfresco meal prepared on the grill, with lovely views of the front lawn and the beautifully kept garden.brbrThe primary bedroom hosts a King bed and a soothing color scheme of grey and white. More natural light floods in, and the mountains act as part of the rooms artwork. The ensuite bath hosts a large rain shower and a separate soaking tub. Truly, this room is a spa-like haven.brbrAs you move downstairs, enjoy the change in vantage point, with the views now being more of the lawn, meadow, and tree line - perfect for spotting birds and other wildlife. Directly at the bottom of the stairs is a door out to the back lawn. The outdoors beckoning beyond.brbrA cozy media room is just to your right, with a lush sectional sofa providing the perfect spot to curl up with your favorite film, or gather around the spacious coffee table for board games or cards. The laundry room is conveniently located at the rear of the media room.brbrJust off the media room is a guest bedroom hosting a queen-sized bed and decked in warm neutral tones. As with all other rooms, this cozy nook has wonderful views and tons of natural light. brbrOn the other side of the landing, a spacious full bath boasts a combination rain shower/soaking tub.brbrJust beyond is a cheery, welcoming kids room, with bunk beds and bright pops of color. A reading nook/”thoughtful spot” offers excellent views of nature and is an excellent spot to plot an adventure.brbrSpacious enough for a group or family, but still cozy enough for a few, come rejuvenate at Mountain View!brbrGuest Access:brWe provide electronic access to the house with a personal guest code. You'll receive the code 24 hours prior to checkin, though your code will only activate at check-in.brbrThe Neighborhood:brWhile this is a perfect respite from the outside world in its tranquil solitude, not far off are the charming towns of Hillsdale NY, Great Barrington MA and Hudson NY. These towns all have great restaurants, shopping, yoga, breweries/distilleries and cultural and historical sites. Visit the house guide for more recommendations!brbrGetting Around:brTo enjoy the expansive beauty of the region, you'll need a car to get here and get around--and the drive will be stunning! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip.brWe strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property, especially in the colder months.

3

Bed

3

Bath

6

Sleeps

$656.54

/ Nightly

Private Vacation Home

Silver Ridge: Hilltop Chalet w/ Sweeping Views

Hillsdale, New York, United States

Summary:brPerched high on the hills above Hillsdale, Silver Ridge is a perfectly-sited contemporary mountain lodge offering sweeping views of the Hudson Valley and total privacy. This stunning property features sunset and mountain views to the west, bathing the interiors in natural light. With 9.8 acres of lawn, mature landscaping, and woods, this secluded haven is just two hours from NYC, providing the perfect escape.brbrThe Space:brThe lodge style interiors features dramatic architecture, including a great room with soaring cathedral ceilings and a stunning ceiling-high stone fireplace, perfect for entertaining family and friends. The space is filled with natural light from large windows and doors, creating bright, inviting spaces with fresh air throughout.brbrThe large gourmet kitchen is a chef's dream, fully equipped with modern appliances, hickory cabinets, plenty of counter space, and an eat-in kitchen island. Adjacent to the kitchen, a spacious dining area with picture windows provides the perfect setting for meals and celebrations.brbrSilver Ridge features four en-suite bedrooms, ensuring that everyone has their own private bathroom. Three bedrooms and all main living spaces are located on the second floor, while one bedroom and bath are on the first floor. A study and work nook near the elevated deck offers the perfect setup for productivity.brbrOutdoor living is unparalleled with a large elevated deck with outdoor dining and a hammock, and a lower level stone terrace with another outdoor dining space with a BBQ grill and an outdoor wood-burning fireplace. These spaces are perfect for barbecues, leisurely afternoons with a good book, or simply soaking in the natural beauty that surrounds you.brbrAdditional features include a TV room/kids' playroom with plenty of space to spread out, and a garage equipped with an EV charger for your convenience. brbrLocated close to Copake Lake, the Taconic State Parkway, Hudson, Great Barrington, Tanglewood, skiing, and all the surrounding area has to offer, Silver Ridge combines amazing design, modern comforts and nature in one exceptional property!brbrThe Neighborhood:brLocated on the NY/Mass border, convenient to all the Berkshire cultural events and skiing to the East, and, to the West, the exciting ambiance of Hudson's art and music world, shopping and fine restaurants. The perfect location for weekend adventures. The thoughtful addition of the computerized generator guarantees peace of mind no matter what the weather brings.brHillsdale is at the nexus of the Berkshires and the Hudson Valley, where you'll find everything from gourmet food and coffee shops, to shopping, yoga, and more. You're also close to hiking in Taconic State Park, the Appalachian Trail, swimming and kayaking in nearby lakes, skiing at Catamount and Butternut, biking, horseback riding, arts, music, cultural institutions, and more.brbrGetting Around:brYou'll need a car to get here and get around and the drive will be beautiful! If arriving from NYC, we recommend taking the Taconic to either exit 54 or exit 72 for the best views. Cell service is good at the house but can be inconsistent in the country, so we recommend that you download the region's online maps to your phone before your trip.

4

Bed

5

Bath

8

Sleeps

$574.6

/ Nightly

Private Vacation Home

Hilltop: Panoramic Views w/ Pool near Catamount

Hillsdale, New York, United States

Summary:brWith 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a contemporary home with complete privacy and everything you need, including a pool, hot tub, fireplaces in the living room, screened porch and guest house. brbrHilltop is between the towns of Great Barrington and Hudson, Catamount Ski Resort is within 10 min, and there are many options for hikes, biking and leaf peeping.brbrThe Space:brAs you approach Hilltop, panoramic views of rolling hills and lush greenery greet you from every angle, setting the stage for an unforgettable retreat.brbrStep inside and discover a light-filled sanctuary where tall ceilings and thoughtful design elements create an atmosphere of effortless elegance and comfort. The main house welcomes you with an open floor plan seamlessly connecting the modern kitchen, dining, and living areas. Relax and unwind in the living room by the fireplace with direct access to the pool deck, where endless summer days await. Whip up gourmet meals in the fully equipped kitchen and dine in style indoors, where another set of large doors opens onto the deck, providing seamless transitions between indoor and outdoor living. Just off the living room, there is a music room, with an ensuite office space.brbrTwo guest bedrooms offer full-sized beds, and there is a full guest bathroom for everyone's convenience. Ascend to the second floor, where the entire level is dedicated to the primary suite—the epitome of comfort boasting awe-inspiring views with a king bed, a spacious bathroom with soaking tub and separate shower, and a walk-in closet.brbrStep outside to Hilltop's sprawling grounds, where endless outdoor enjoyment awaits amidst spectacular views and breathtaking sunsets. The courtyard oasis features a pool, a hot tub, outdoor dining and lounging and an outdoor shower. Off of the patio, a screened in porch complete with its own fireplace is perfect for cozy evenings. With Catamount Ski Resort just minutes away and a variety of hiking, biking, and leaf-peeping options nearby, Hilltop is the perfect destination for outdoor enthusiasts and nature lovers alike.brbrSouth of the main house, the charming guest house offers a private haven with a kitchenette, living area, wood-burning stove, full bath, and bedroom, along with a private deck, perfect for unwinding amidst the natural beauty. The bedroom has a queen bed and a full size sofa bed.brbrEscape to Hilltop and experience the epitome of comfortable country living, where every amenity and comfort awaits amidst breathtaking natural beauty. This is more than just a home; it's a lifestyle of unparalleled comfort and tranquility.brbrGuest Access:brWe provide electronic access to the house with a personal guest code. You'll receive the code 24 hours prior to checkin, though your code will only activate at check-in.brbrThe Neighborhood:brHilltop, the perfect respite from the outside world in it’s tranquil solitude. However, not far off is the charming town of Hillsdale NY, Great Barrington MA and Hudson NY. These towns all have great restaurants, shopping, yoga, breweries/distilleries and cultural and historical sites. Visit the house guide for more recommendations!brbrGetting Around:brTo enjoy the expansive beauty of the region, you'll need a car to get here and get around and the drive will be stunning! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip. We strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property in winter.

Bed

Bath

Sleeps

$228.6

/ Nightly

Cabin

magical cabin in the woods

Hillsdale, New York, United States

Our ‘Cabin in the Woods’ can be described in many different ways, but simply put it’s nothing short of MAGICAL. Tucked away near a babbling stream, this rustic, romantic cabin surrounded by lush oak and maple trees is the best backdrop for your home away from home. Located just 5 miles from Catamount Mountain Resort, this is the perfect getaway for couples and groups up to 6 people. The Cabin is perfectly secluded but the charming Book Barn is only a short 300 feet away which makes it feel that you are not completely alone in the wilderness.

2

Bed

2

Bath

6

Sleeps

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