Vacation Rentals By Owner In Hillsdale, NY

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, 1 exterior security camera (facing front porch)brACCESSIBILITY: Stairs required for entry & 2nd-floor bedroom accessbrPARKING: 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- 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

Waterfalls and Trails at 'The Mills At Green Hole'

Hillsdale, New York, United States

6

Bed

Bath

15

Sleeps

$8102.47

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!

The Brooks Buy Out, Wedding Groups Inquire Today!

Hillsdale, New York, United States

Bed

Bath

Sleeps

$561.61

Escape to the 1850s Bell House, a historic 5BR/4.5BA estate in Hillsdale NY, once home to the prominent Bell family. Set on 3.6 acres, this fully restored gem blends period charm with modern luxuries like central A/C, heating & WiFi. Enjoy a large private swimming pool, cozy patio & ample space for the whole family. Walk to town for dining, galleries, boutiques & farmers markets. Perfect for unforgettable family getaways in a timeless countryside setting. Additional 2 person studio available.brbrOur home sleeps up to 10 guests.brbr★★ Luxurious Bedrooms for Every Guest ★★br➤ Master Bedroom Suite (1st Floor): Spacious main-level suite with a queen bed, large windows, and patio doors that open to the backyard. Includes a private en suite bathroom with a custom-tiled stand-up shower.brbr➤ North East Bedroom (2nd Floor): Bright front-facing bedroom on the 2nd floor with a queen bed, three windows and a closet. Enjoy natural light and views of the front and side yards.brbr➤ North West Bedroom (2nd Floor): Quiet 2nd floor queen bedroom with backyard views and direct access to a private en suite bathroom featuring a full bathtub.brbr➤ South East Bedroom (2nd Floor): Cozy corner 2nd floor bedroom with a full size bed, two windows and access to a full Jack and Jill bathroom with a stand-up shower. Overlooks the front and side yards.brbr➤ South West Bedroom (2nd Floor): Tucked toward the back of the home, this full bed room features two windows with side and backyard views, plus access to a full Jack and Jill bathroom with a stand-up shower.brbr★★ Spacious Living & Entertainment Areas ★★br➤ Living Room: Expansive and inviting, this sun-drenched living room features a large sectional sofa, additional seating, floor-to-ceiling windows and a big-screen Roku TV - perfect for relaxing or gathering with the whole family.brbr➤ Gourmet Kitchen: This oversized kitchen comes fully stocked with stainless steel appliances, an island for prep or conversation and all the cookware you need. Includes a cozy breakfast table for casual meals.brbr➤ Elegant Dining: Host unforgettable dinners at the custom-built solid wood dining table with comfortable seating for 10 or more guests.brbr★★ Outdoor Amenities ★★br➤ Private Pool: Take a dip in your own oversized swimming pool - perfect for cooling off or enjoying long summer days (open seasonally May to September) brbr➤ Back Patio: Spacious gravel patio accessible from the kitchen, laundry room and master bedroom. Includes an outdoor dining set and overlooks the backyard and private pool.brbr➤ Propane Grill: Fire up the 4-burner propane grill for laid-back BBQs and outdoor feasts.brbr➤ Grassy Lawn: Expansive, shaded lawn - ideal for lounging, playing, or picnicking under the trees.brbr➤ Front Porch: Welcoming and covered, the spacious wrap around front porch features classic Adirondack chairs - perfect for morning coffee or relaxing with a good book.brbr★★ Local Attractions & Approximate Driving Times ★★br★ Family Fun ★br➤ Hillsdale General Store - 1 minbr➤ Nobletown Fiber Works - 1 minbr➤ Catamount Aerial Adventure Park - 5 minbr➤ Hornets Nest Xtreme Paintball - 20 minbr➤ Columbia County Fair Grounds - 25 minbr➤ Lebanon Valley Speedway - 35 minbr➤ Trevor-Lovejoy Zoo - 37 minbr➤ Ramblewild Aerial Adventure Park - 43 minbr➤ Zoom Flume Water Park - 53 minbrbr★ Historical / Cultural ★br➤ LABspace Gallery - 1 minbr➤ Copake Iron Works Historic Site - 8 minbr➤ Rodgers Book Barn - 9 minbr➤ Mahaiwe Performing Arts Center - 17 minbr➤ Crandell Theatre - 23 minbr➤ FASNY Museum of Firefighting - 24 minbr➤ Art Omi Sculpture Park - 27 minbr➤ Norman Rockwell Museum - 29 minbr➤ The Unicorn Theatre - 30 minbr➤ Olana State Historic Site - 31 minbr➤ Naumkeag Gardens - 31 minbr➤ Tanglewood Music Center - 31 minbr➤ Hancock Shaker Village - 32 minbr➤ Animagic Museum of Animation Special Effects & Art - 32 minbr➤ The Mount | Edith Wharton's Home - 34 minbr➤ Old Rhinebeck Aerodrome - 40 minbr➤ Jacob's Pillow - 44 minbrbr★ Hiking & Nature ★br➤ Roeliff Jansen Park - 2 minbr➤ Taconic State Park - 7 minbr➤ Rheinstrom Hill Audubon Sanctuary - 9 minbr➤ Bash Bish Falls State Park - 10 minbr➤ Race Brook Falls - 16 minbr➤ High Falls Conservation Area - 17 minbr➤ Guilder Pond - 21 minbr➤ Housatonic Flats Reserve - 21 minbr➤ Monument Mountain Reservation - 24 minbr➤ Bartholomew's Cobble Reservation - 24 minbrbr★ Water Sports ★br➤ Copake Lake Boat & Ski - 8 minbr➤ Mickey's Marina - 9 minbr➤ Lake Taghkanic State Park Beach & Boat Rental - 24 minbr➤ O'Hara's Landing Marina - 29 minbr➤ Screaming Eagle Outdoor Adventures - 37 minbrbr★ Ski Resorts ★br➤ Catamount Mountain Ski Resort - 5 minbr➤ Ski Butternut - 24 minbr➤ Bousquet Mountain Ski Area - 35 minbrbr★ Food & Beverage ★br➤ Sweet Peas Country Diner - 1 minbr➤ Hillsdale House - 1 minbr➤ Cook & Larder - 1 minbr➤ Roe Jan Brewing Co. - 2 minbr➤ Twisted Sisters Coffee House - 2 minbr➤ Four Brothers Pizza Inn - 3 minbr➤ Zinnia’s Dinette - 4 minbr➤ Little Apple Cidery - 5 minbr➤ Little Cat Lodge - 5 minbr➤ Hy's Fried - 5 minbr➤ Copake General Store & Deli - 8 minbr➤ Dad's Copake Diner - 8 minbr➤ Mom's Country Cafe - 9 minbr➤ The Mill - 9 minbr➤ The Greens at Copake Country Club - 10 minbrbr★ Convenience / Grocery Stores ★br➤ Stewart's Shops - 1 minbr➤ Gulf Express - 1 minbr➤ Freshtown - 2 minbr➤ Hillsdale Fine Wine & Spirits - 2 minbrbr★ Farm Fresh ★br➤ Copake Hillsdale Farmers Market - 2 minbr➤ Vine Gate Lavender Floral Farm - 2 minbr➤ Hawthorne Valley Farm Store - 13 minbr➤ Philmont Cooperative - 15 minbr➤ Thompson-Finch Farm - 16 minbr➤ Guido's Fresh Marketplace - 16 minbr➤ Berkshire Food Co-op - 17 minbr➤ Hudson Farmers Market - 21 minbr➤ Hilltop Orchards - 26 min

Giant Historic 1850s Berkshires Retreat Bell House @ Hillsdale, NY Town Center

Hillsdale, New York, United States

5

Bed

Bath

10

Sleeps

$1125.33

The Old Oak Residence is located in a charming town between Hudson NY and Great Barrington MA, just over 2 hours from New York City. The property has over 8 acres with grassy yard, woods, multiple streams, pond, and barns to explore, offering 4 bedrooms and 3 full bathrooms over two floors, with a mix of antiques and modern decor. On the ground floor, there is a large mudroom with a new Vermont Castings wood burning stove, full bathroom, and space for coats, boots, and sporting equipment. The central living areas include an inviting living room with library and French doors leading to the back stone patio as well as a double-sided fireplace connecting to a formal dining room that seats 8. There is a new kitchen with top-of-the-line range, refrigerator, dishwasher, microwave, and espresso machine as well as cooking equipment, dishware, stemware, tableware, and utensils. The kitchen has a large island for meal preparation along with a table for 6, a Vermont Castings wood burning fireplace, and French doors leading to the back stone patio which has a grill and table for alfresco dining. Upstairs, the home has a primary bedroom with queen mahogany four poster bed, tv, walk-in closet, and ensuite bathroom with large bathtub; a second spacious, light-filled bedroom with queen modern four poster bed; a serene third bedroom with queen bed and custom headboard; and a well-appointed fourth bedroom with 2 twin beds. There is a shared full bathroom, laundry room with washer and dryer, and large activity room with tv, couch, chairs, table, and daybeds. Each bedroom comes with linens, blankets, and towels.

The Old Oak Residence: Luxury Rental in The Hudson Valley / Berkshires

Hillsdale, New York, United States

Bed

Bath

8

Sleeps

$452.54

Escape to this private Hillsdale retreat featuring two full living spaces with separate entrances and kitchens — perfect for families and groups. Set on a lush, peaceful property with a koi pond, this home offers comfort, space, flexibility, and ultimate privacy just minutes from Catamount, Hudson, and the Berkshires. Relax, reconnect, and enjoy effortless Hudson Valley.brbrWelcome to your private Hillsdale escape — a spacious, tucked-away retreat designed for connection, flexibility, and relaxed Hudson Valley living.brbrInside, the home offers a rare and highly desirable layout with two separate living levels, each with its own entrance, kitchen, and living space. Perfect for multiple families or groups, this setup allows everyone to spread out comfortably while still gathering together.brbrThe home is surrounded by a peaceful, wooded setting with a charming koi pond, creating a calm and private atmosphere from the moment you arrive. Natural light, comfortable furnishings, and thoughtful layout make it easy to settle in and feel at home.brbrStart your mornings with coffee overlooking the trees. Spend your days exploring nearby hiking trails, cultural destinations, and charming towns across the Hudson Valley and Berkshires. In winter, you’re just minutes to Catamount Ski Area, while warmer months invite outdoor adventures, local farms, and long, relaxed evenings.brbrWith space for groups and a layout designed for flexibility, this home is ideal for families, couples, and friends traveling together.brbrThis home is currently available for a limited offering in July, August, and February. Please inquire about additional dates, as there may be flexibility.

Hudson Valley Private Retreat with 3 bedrooms, 2 living spaces, and a pond.

Hillsdale, New York, United States

Bed

Bath

Sleeps

$907.2

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.brbrSECURITYbrFor security, there is a ring camera on the exterior of the main entrance. There are no other cameras inside your Wander home.brbrCONSTRUCTION NOTICEbrThis home is in a growing neighborhood, with new homes being built, so you may hear or experience construction sounds from these neighboring properties during weekdays, until 6 PM. Some construction may also obstruct the views from the home. Wander Concierge is happy to answer any questions or concerns.brbrSAFETY NOTICEbrBurn Ban AwarenessbrDue to ongoing dry weather, several local towns may implement a burn ban. Check conditions in the area before your trip, and please remain FIRE AWARE, as gusty winds and extremely dry conditions can pose a heightened risk. We recommend refraining from any outdoor burning during dry periods until conditions improve with anticipated rain.brbrLAKE ACCESSbrThe nearby lake is for viewing and recreation only — swimming is not permitted.brbrPET FRIENDLYbrMost Wander homes are pet-friendly, and we’re happy to welcome your furry companions during your stay. We allow a maximum of two dogs per reservation for this property, with a flat pet fee of $350/stay charged at check-out, regardless of whether you bring one or two dogs. brbrNo cats are allowed inside the home to maintain a hypoallergenic area as much as possible for those with sensitivities.brbrThis fee goes directly to our cleaners to cover the additional work required after a pet stay. Please note that the pet fee does not cover any damage caused by pets or violations of the pet policy.brbrNO SMOKINGbrSmoking is strictly prohibited both inside and outside the home. A fine of $1,000 will be applied to any guest found violating this policy.brbrEVENTS brNo events allowed.

Hillsdale Lakeside / Lake Access, Balcony & BBQ

Hillsdale, New York, United States

Bed

Bath

Sleeps

$498.17

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!

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale, New York, United States

Bed

Bath

Sleeps

$272.16

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.

Country House

Private Unit in shared 1830 Farmhouse

Hillsdale, New York, United States

Bed

Bath

Sleeps

$224.0

Located in the heart of the Berkshires, equidistant from NYC and Boston, this newly equipped and renovated carriage house is located in the historic town center of Hillsdale, NY. The carriage house is a completely separate and private structure from the main house. You'll have a Swiss chalet-style, warm spacious living room, a cozy dining room with a wooden table fit for 6, a fully equipped quaint kitchen with modern conveniences (with pots/pans, dishes and silverware, coffee maker, dishwasher, toaster oven and microwave), bathroom with washer/dryer, balcony with beautiful view of Catamount, 2 spacious bedrooms downstairs with built-in closets (one with a queen bed, the other with 2 twins). Additional sleeping space for two is located in the living room (queen pull-out sofa). There are exposed beams from the original barn throughout the house. The entrance has a solarium/mudroom for skis, boots, shoes, hiking boots, golf clubs, and bikes (bring your own). There is a lovely decorative Vermont Castings stove in the living room. There is internet and Roku TV. Our driveway can hold up to 2 guest cars. Perfect for year-round getaways. Our guest house has easy access to all that the Berkshires, Western Massachusetts, and the Hudson Valley has to offer. You will have access to the 2.7 acres of land which are partially wooded and partially grass and include a blueberry patch, Macintosh and Golden Delicious apple tree, and blackberries which you can enjoy depending on the season.brbrYou’ll be five minutes walking distance from the Hillsdale supermarket, a wine and spirit store, Hillsdale House Restaurant, O’s Country Diner, Mount Washington House Grill, Hillsdale General Store, Home Chef, playground for the kids, Cobble Pond Farms Gulf station, Crossroads Restaurant, Stewart’s shop, Village Scoop Ice Cream, post office, Passiflora gift store, Taconic Valley Bicycle and Hiking Rail Trail and the Roe Jan Brewing Company. Further, you are within five minutes car ride to Catamount Ski area/Catamount Adventure park, the local library, Roeliff Jansen Park (nature preserve walk, home of the Copake/Hillsdale farmer’s market) and Four Brothers Pizza Inn Restaurant. You are within a 10 minutes’ drive to Bash Bish waterfall, Copake Lake Country Club and Egremont Country Club (gulf) and Taconic State Park (swimming). Hudson and Great Barrington are within 25- and 20-minutes drive respectively. Butternut Ski area is within a 25 minutes’ drive. Tanglewood is 30 minutes away. Norman Rockwell Museum is 30 minutes away as well. Millerton Cascade Mountain Vinery is 30 minutes away. Mac-Haydn Theatre is 25 minutes away. Hancock Shaker Village is 35 minutes away. Jacob’s Pillow Dance Center is within 46 minutes away.

Chalet

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

Hillsdale, New York, United States

Bed

Bath

Sleeps

$205.96

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.

Country Karma -Quiet Wooded Getaway

Hillsdale, New York, United States

Bed

Bath

10

Sleeps

$337.48

Canoe & Paddleboard | Bright, Airy Interior | Year-Round AppealbrbrSet on the county's largest motorized lake, this vacation rental in Hillsdale offers comfort and classic Upstate charm. Enjoy coffee on the deck overlooking the Copake Lake, afternoons boating, and evenings by the fire pit under the stars. You can also explore Bash Bish Falls, hike the Taconic Range, or spend winter days at Catamount. Then, return to the home — complete with 1 bedroom and 1 lofted sleeping area. You deserve this!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom: 1 queen bedbr- Loft: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrOUTDOOR LIVINGbr- Boat dock w/ lake accessbr- Canoe & paddleboard, life vestsbr- Wood-burning fire pit (bring your own wood)br- Charcoal grillbr- Furnished deckbrbrMAIN FEATURESbr- Smart TVbr- Board games & booksbr- Stereobr- Dining table & breakfast barbrbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Microwave, toaster, blenderbr- Drip coffee makerbr- Cooking basics, spicesbr- Dishware/flatwarebr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Washer/dryer (detergent provided)br- Central A/C & heating, ceiling fanbr- Linens, bath & lake towelsbr- Complimentary toiletriesbr- Hair dryerbr- Keyless entrybrbrFAQ br- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- Single-level home w/ loftbr- Steps to enterbrbrPARKINGbr- Driveway (3 vehicles)brbr-- THE LOCATION --brbr- Located on Copake Lake: the largest motorized lake in Columbia Countybr- 2 miles to Copake Lake Boat & Ski: daily boat rentals, kayaks, bar, restaurants, live music during summerbr- 2 miles to Copake Country Club: public 18-hole golf coursebr- 7 miles to Taconic State Parkbr- 9 miles to Bash Bish Falls State Parkbr- 10 miles to Catamount Mountain Resortbr- 17 miles to Hudsonbr- 18 miles to Great Barrington, MAbr- 20 miles to Olana State Historic Sitebr- 57 miles to Albany Int'l Airportbrbr-- 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- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-level home with a loft requires steps to enterbr- Your safety matters. This property features 1 exterior security camera located on the front of the house, facing outward toward the exterior entry/driveway. The camera records video and sound when activated by motion

Lakefront Escape w/ Dock! Hudson Valley Home

Hillsdale, New York, United States

2

Bed

1

Bath

6

Sleeps

$870.05

Your Dream Upstate Country Escape Awaits!brbrWelcome to your private Hudson Valley getaway — a newly remodeled 3-bedroom, 3-bathroom home that blends modern luxury with natural beauty. Tucked away at the end of a quiet dead-end road on 13 peaceful acres, this stylish retreat offers the perfect balance of seclusion and comfort.brbrStep inside to find high-end appliances, elegant fixtures, and thoughtfully designed spaces that make every stay feel special. The open-concept living area is bright and inviting, ideal for relaxing with family or entertaining friends.brbrThe walk-out basement adds extra space for gathering, games, or quiet downtime — with beautiful views of the surrounding countryside.brbrWhether you’re sipping coffee on the deck, exploring local trails, or simply unwinding in the peaceful landscape, you’ll love the sense of privacy, calm, and connection to nature this home provides.brbrWe look forward to hosting you and helping you experience the best of Upstate living!brbrPLEASE NOTE:brThis is our personal residence, which we live in full time with our two daughters. Hosting and managing vacation homes locally is our career, so we’ve thoughtfully set up our home for guests to enjoy while we’re away.brbrWe only rent this property during Thanksgiving and for a few weeks in the summer, but please feel free to reach out if you’re interested in other times — we occasionally open our home during school breaks when we take mini getaways.

Private 13-Acre Escape — Renovated 3BR Home with Stunning 360° Views

Hillsdale, New York, United States

Bed

Bath

Sleeps

$186.69

Escape to the 1850s Carriage House - a charming 1-bedroom studio tucked inside a restored barn on a historic Hillsdale, NY estate, once home to the prominent Bell family. This beautifully renovated gem combines period character with modern comforts including central A/C, heating & WiFi. Relax in the cozy studio, unwind on the private patio w/ a BBQ grill & enjoy easy walks to town for dining, shops & farmers markets. A perfect blend of history and comfort for a memorable countryside getaway.brbr★★ The Space ★★br➤ Thoughtfully restored with modern comforts, including WiFi, air conditioning and heating for year-round enjoyment.brbr➤ Relax on a cozy queen-size bed with soft linens for a great night’s sleep.brbr➤ Enjoy meals or morning coffee at the intimate table with seating for two.brbr➤ Modern full bath featuring a custom-tiled stand-up shower and fresh towels.brbr➤ Compact and convenient kitchenette with a mini fridge, sink, microwave, coffee and hot water kettle - everything you need for simple meals and snacks.brbr➤ Unwind on the grassy lawn with outdoor furniture perfect for al fresco dining or lounging in the fresh air.brbr➤ Fire up the propane BBQ grill and enjoy a laid-back outdoor meal.brbrPlease note that a larger rental home with a private pool is located on the same property. If booked during your stay, there may be occasional noise. We kindly ask all guests to respect quiet hours and be mindful of neighbors, so everyone can enjoy a peaceful and relaxing environment.brbr★★ Local Attractions & Approximate Driving Times ★★br★ Family Fun ★br➤ Hillsdale General Store - 1 minbr➤ Nobletown Fiber Works - 1 minbr➤ Catamount Aerial Adventure Park - 5 minbr➤ Hornets Nest Xtreme Paintball - 20 minbr➤ Columbia County Fair Grounds - 25 minbr➤ Lebanon Valley Speedway - 35 minbr➤ Trevor-Lovejoy Zoo - 37 minbr➤ Ramblewild Aerial Adventure Park - 43 minbr➤ Zoom Flume Water Park - 53 minbrbr★ Historical / Cultural ★br➤ LABspace Gallery - 1 minbr➤ Copake Iron Works Historic Site - 8 minbr➤ Rodgers Book Barn - 9 minbr➤ Mahaiwe Performing Arts Center - 17 minbr➤ Crandell Theatre - 23 minbr➤ FASNY Museum of Firefighting - 24 minbr➤ Art Omi Sculpture Park - 27 minbr➤ Norman Rockwell Museum - 29 minbr➤ The Unicorn Theatre - 30 minbr➤ Olana State Historic Site - 31 minbr➤ Naumkeag Gardens - 31 minbr➤ Tanglewood Music Center - 31 minbr➤ Hancock Shaker Village - 32 minbr➤ Animagic Museum of Animation Special Effects & Art - 32 minbr➤ The Mount | Edith Wharton's Home - 34 minbr➤ Old Rhinebeck Aerodrome - 40 minbr➤ Jacob's Pillow - 44 minbrbr★ Hiking & Nature ★br➤ Roeliff Jansen Park - 2 minbr➤ Taconic State Park - 7 minbr➤ Rheinstrom Hill Audubon Sanctuary - 9 minbr➤ Bash Bish Falls State Park - 10 minbr➤ Race Brook Falls - 16 minbr➤ High Falls Conservation Area - 17 minbr➤ Guilder Pond - 21 minbr➤ Housatonic Flats Reserve - 21 minbr➤ Monument Mountain Reservation - 24 minbr➤ Bartholomew's Cobble Reservation - 24 minbrbr★ Water Sports ★br➤ Copake Lake Boat & Ski - 8 minbr➤ Mickey's Marina - 9 minbr➤ Lake Taghkanic State Park Beach & Boat Rental - 24 minbr➤ O'Hara's Landing Marina - 29 minbr➤ Screaming Eagle Outdoor Adventures - 37 minbrbr★ Ski Resorts ★br➤ Catamount Mountain Ski Resort - 5 minbr➤ Ski Butternut - 24 minbr➤ Bousquet Mountain Ski Area - 35 minbrbr★ Food & Beverage ★br➤ Sweet Peas Country Diner - 1 minbr➤ Hillsdale House - 1 minbr➤ Cook & Larder - 1 minbr➤ Roe Jan Brewing Co. - 2 minbr➤ Twisted Sisters Coffee House - 2 minbr➤ Four Brothers Pizza Inn - 3 minbr➤ Zinnia’s Dinette - 4 minbr➤ Little Apple Cidery - 5 minbr➤ Little Cat Lodge - 5 minbr➤ Hy's Fried - 5 minbr➤ Copake General Store & Deli - 8 minbr➤ Dad's Copake Diner - 8 minbr➤ Mom's Country Cafe - 9 minbr➤ The Mill - 9 minbr➤ The Greens at Copake Country Club - 10 minbrbr★ Convenience / Grocery Stores ★br➤ Stewart's Shops - 1 minbr➤ Gulf Express - 1 minbr➤ Freshtown - 2 minbr➤ Hillsdale Fine Wine & Spirits - 2 minbrbr★ Farm Fresh ★br➤ Copake Hillsdale Farmers Market - 2 minbr➤ Vine Gate Lavender Floral Farm - 2 minbr➤ Hawthorne Valley Farm Store - 13 minbr➤ Philmont Cooperative - 15 minbr➤ Thompson-Finch Farm - 16 minbr➤ Guido's Fresh Marketplace - 16 minbr➤ Berkshire Food Co-op - 17 minbr➤ Hudson Farmers Market - 21 minbr➤ Hilltop Orchards - 26 min

Restored Historic 1850s Barn Carriage House Studio @ Hillsdale Town Center

Hillsdale, New York, United States

1

Bed

1

Bath

2

Sleeps

$718.93

Located in Hillsdale, this gorgeous house offers a comfortable retreat for guests. With two bedrooms featuring a queen bed, a bunk bed, a twin bed, and a Murphy bed, there’s plenty of space for everyone to relax. Two bathrooms add convenience for families or groups. The home stays cozy with heating and cool with AC, making it perfect year-round. Guests will appreciate thoughtful touches like a hair dryer to make packing easier. Whether you’re unwinding indoors or exploring nearby, this quaint house provides a phenomenal base for your getaway. Enjoy all that Hillsdale has to offer when you stay at our place.

Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale, New York, United States

Bed

Bath

Sleeps

$1751.68

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,

Chef’s Kitchen, Fast Wi-Fi

Hillsdale, New York, United States

5

Bed

Bath

14

Sleeps

$375.8

Discover this delightful 3-bedroom gem in Hillsdale. This lovely house features 1 king bed and 2 queen beds, perfect for a comfortable stay. With 4 bathrooms including a jetted bathtub, guests can relax and unwind. Enjoy amenities like WiFi, AC, and a washing machine. Plus, there's an additional office space with a full bed for extra convenience. We think our place will help you experience everything Hillsdale has to offer.

3-bedroom house in fantastic Hillsdale with mountain views, WiFi, AC

Hillsdale, New York, United States

Bed

Bath

Sleeps

$560.33

Escape the city and relax at our serene Hillsdale House, nestled alongside a picturesque creek and pond with acres of shady woods to hike and explore. Cozy nooks abound to decompress with your favorite book. The home is WFH and remote learning equipped with 1GB internet and several quiet spaces for work, zoom, art projects... you name it! brbrA quick 2.5hr trip from NYC. 5mins to historic Hilldale, 15mins to Great Barrington, 30mins to the Hudson Amtrak station. 10 Mins to Catamount slopes!brbrIn addition to all the typical amenities and aesthetics you want in a vacation home, you will ALSO find:br- marked hiking trail on the property (including search for 6 fairy doors)br- NO pictures of someone else’s family br- empty drawers... waiting for your clothing!br- clutter FREE spacebr- iOS chargers in all bedroomsbr- work friendly spaces... feel free to plug in if and when you want tobr- serious WiFi: It is just as good as our WiFi in Brooklyn... WiFi extends outside... AND it still works on the porch and we have even had successful facetimes in the backyard. brbrMore details on the rooms are below. We are new hosts, but we have stayed at some pretty sweet places and have a good understanding of what works and are learning along the way!brbrMain Floor: brSpacious chef's kitchen complete with double ovens, dishwasher and plenty of counter space. Large dining room is perfect for entertaining and gathering with family/friends and contains a newly renovated half-bath (powder room). The light filled living room boasts a working fireplace and plenty of room for gathering with loved ones, yoga, chess, reading, napping, chilling etc. The adjoining screened-in porch is the perfect place to breath fresh air and relax. Turn on the outdoor ceiling fan for a perfect breeze on a hot day!brbrLower Level: brSnuggle up and chill or watch your favorite movies on the flat screen Samsung Frame TV. Enjoy the adjoining light filled art/zoom room… great for art projects, playing, remote learning etc. The lower level also leads out to the streamside patio area, which is ready for al fresco dining, grilling on the large Weber Genesis grill and gathering safely outdoors. brbrUpstairs: br4 tranquil bedrooms await… BR 1: King Bed, plenty of closet space, listen to the tranquil sounds of the neighboring stream as you drift off to sleep. BR 2: Light filled room with Queen Bed and tons of charm. BR 3: A perfect room for kids or guests with 2 Twin beds (plus additional trundle bed) and space to play. BR 4: This room has a twin daybed (might be the coziest spot in the entire house) as well as a lovely desk area complete with dual monitor setup… just in case you need to check in with the office while away. 2 freshly renovated full bathrooms finish out the upper level, which providing options of a walk-in shower with glass surround OR a lovely deep soaking tub for relaxing after a long day. brbrSmart Home Featuresbr• 3 Nest Thermostats control the baseboard heating systembr• Phillips Hue Lighting on main and lower levelsbr• Newly installed ADT Security System

Serene Hillsdale Cottage Amped with Tech and Wifi

Hillsdale, New York, United States

Bed

2

Bath

8

Sleeps

$431.2

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.

Meadowland Farmhouse with Beautiful Sunsets 5 minutes from town

Hillsdale, New York, United States

Bed

Bath

Sleeps

$836.58

Summary:brbrPerched 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 2.5 hours from NYC & Boston, providing the perfect escape.brbrbrbrThe Space:brbrThe 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.brbrbrbrThe 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.brbrbrbrSilver 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.brbrbrbrOutdoor 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.brbrbrbrAdditional 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. brbrbrbrLocated 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!brbrbrbrThe Neighborhood:brbrLocated 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.brbrHillsdale 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.brbrbrbrGetting Around:brbrSilver Ridge is approx. 2.5 hours from Boston and New York City. You'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.

Silver Ridge: Hilltop Chalet w/ Sweeping Views

Hillsdale, New York, United States

Bed