Vacation rentals in Spencertown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Spencertown

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Superhost

A charming porch welcomes guests with its white railing and a mix of potted plants. Two green doors provide entry to the home, while a table and chairs invite relaxation. Shade is offered by the surrounding trees, enhancing the outdoor space.

Apartment in Philmont

4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

Enjoy the elegant ambience of this airy and bespoke space, just two doors up from the excellent restaurant Local 111, as well as the Co-op, where you can pick up delicious local produce, meats, and baked goods. A couple blocks from the Philmont Pub, another fantastic place to eat and enjoy the evenings. Minutes from Hudson, this town is literally in the center of Columbia County. A short drive to Catamount, Bash Bish, the Hudson River, the Catskills, the Berkshires, no end of places to explore!

Top guest favorite

A sunken fire pit area is illustrated, surrounded by wooden walls and adorned with potted plants. Four red Adirondack chairs are positioned around a circular fire pit, set on a stone patio. A secure black fence encloses the space, providing privacy.

Home in Craryville

4.92 out of 5 average rating, 119 reviews

The Gatehouse at Raspberry Ridge

Quiet, private house for a country get-away. Renovated 2 bedroom, 1 bath home can sleep up to 2 couples. Gated and fenced yard offers privacy and security for children or dogs. Enjoy a spacious deck and sunken fire pit for outdoor dining or lounging. Bedrooms and living space upstairs are bright, airy with cozy wood stove for cool evenings. Kitchen is well-stocked; has a dishwasher. Laundry facilities downstairs; entertainment room with large screen TV and pull out couch. WiFi available.

Guest favorite

A sunlit sunroom showcases large windows offering views of the surrounding forest. A comfortable sofa is complemented by a colorful throw, with a rustic coffee table positioned in front. Vintage lamps provide soft lighting, enhancing the cozy atmosphere of this inviting space.

Cabin in Chatham

4.91 out of 5 average rating, 130 reviews

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House is surrounded by acres of forest and is close to conservation areas with hiking trails. Minutes to antiquing, Kripalu, Norman Rockwell Museum, The Mount, Tanglewood, Skiing, Shakespeare & Co. You’ll love my place because of the peace, quiet and seclusion. Located up an old dirt country road. Relax by the wood stove (bring wood), in the sun room or explore nearby Spencertown, Chatham or West Stockbridge. Many ski slopes nearby & a small lake! If visiting in winter, 4wd recommended.

Top guest favorite

The chalet is set among trees, featuring a wooden exterior and a spacious deck adorned with warm lights. The two-story structure includes a balcony on the upper level and large windows inviting natural light. A garage is visible to the right, situated on a green lawn.

Cabin in Ghent

4.99 out of 5 average rating, 268 reviews

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom (5-beds), 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features an open floor plan, luxury bathrooms, new, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. The home is surrounded by nature—trees, trails, streams, and farms—all close by. Hike, bike, kayak, or go to a brewery. Discover the nearby Hudson Valley farms, ski in the Berkshires, or visit the trendy town of Hudson, NY.

Top guest favorite

A well-lit hallway is shown, leading towards a staircase with polished wooden steps and a black handrail. A decorative rug is positioned at the entrance, and doors are visible along the walls, adding a sense of depth to the space.

Guesthouse in Great Barrington

4.96 out of 5 average rating, 124 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Guest favorite

The Chatham House is captured at night, showcasing its distinct architecture with a spacious balcony adorned with lights. An American flag waves gently, while illuminated signs indicate open establishments nearby. Surrounding greenery and decorative elements enhance the inviting façade.

Home in Chatham

4.89 out of 5 average rating, 186 reviews

Chatham Villg Walk to Main. 100% Smoke/Animal Free

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to Main St pubs/pizza/movies/fine dining shopping 12mi Hudson Amtrak (taxi, Uber avail). Town park w/swim pond & tennis courts half-mile. Tanglewood 24mi. Keyless entry. Host on premises always available. 100% smoke/pet-free property. Check-in 4pm/-out 11a. 55" Sony TV. Free high-speed WiFi. Fully stocked home. Private outdoor dining w/propane bbq. 2 guests max for ultimate comfort. Park @ door. See more details within

Guest favorite

A wooden porch features structural beams and railings, providing a welcoming entrance to the house. Surrounding greenery includes trees and low-growing plants, creating a natural and shaded ambiance. The exterior is painted in a dark tone, complemented by red doors, enhancing the structure's character.

Home in Chatham

4.89 out of 5 average rating, 171 reviews

Country house on Indian Creek

Tucked away in a beautiful valley, this house is surrounded by farm hills and creeks. Located on 5 acres of grassland and 10 acres of woodland. Close to 3 ski mountains, 2 lakes, and tons of hiking and mountain biking trails. Very peaceful and spacious place to unwind. Just 5 minutes away from town center but feels miles away from everything. If you open my profile picture you will find my guidebook, which gives you a idea of some places to eat and attractions around the area.

Top guest favorite

The image displays a green sign for the Mt. Washington House featuring gold lettering. The sign indicates parking to the right and notes 'No Vacancy.' Wet pavement reflects the surroundings, with a glimpse of greenery and buildings in the background.

Apartment in Hillsdale

4.99 out of 5 average rating, 208 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Top guest favorite

The exterior of the tiny house is presented, featuring a sleek, modern design with large windows allowing natural light. A spacious deck made of wooden planks leads to a seating area with a table and chairs, surrounded by open fields and trees.

Tiny home in Chatham

4.99 out of 5 average rating, 243 reviews

Tiny House, Big Adventure on 70 acres

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Guest favorite

A small table with a bronze metal base and a wooden top is set beside a gently flowing stream. A wrought iron chair accompanies the table, surrounded by lush greenery. The area features a peaceful woodland backdrop, enhancing the sense of nature.

Home in Chatham

4.9 out of 5 average rating, 237 reviews

Pet-friendly. Private. Host leans left. F Trump.

This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

Guest favorite

A spacious wooden deck extends from the cabin, surrounded by trees showcasing autumn foliage. Two chairs are placed on the deck, facing the tranquil wooded landscape, providing a serene spot to enjoy nature.

Cabin in Chatham

4.97 out of 5 average rating, 131 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Top guest favorite

Three decorative ceramic figures are positioned on a countertop, their colorful designs creating a cheerful focal point. Two white mugs are visible nearby, alongside a white utensil holder that contains various kitchen tools. Natural light filters through a window, enhancing the vibrant hues of the figures.

Tiny home in Chatham

4.99 out of 5 average rating, 414 reviews

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Spencertown vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Spencertown

Top guest favorite

The exterior of a rustic barn-style guest house is surrounded by lush trees and greenery. A warm red door is framed by a covered porch, and the structure features a classic green metal roof. Natural stone pathways lead towards the entrance.

Home in Ghent

5 out of 5 average rating, 27 reviews

Hawthorne Valley Barn

CristinaRating, 5 stars3 months ago

Our stay at Kim's home upstate was absolutely perfect! The accommodations were exactly as described and super clean. If you're looking for a quaint, cozy unique experience this is it! We had all we needed and communication was easy and pleasant. Highly recommend

Top guest favorite

A wooden deck is surrounded by lush greenery, overlooking a serene natural landscape. Outdoor seating is provided, featuring a coffee table and comfortable chairs. A grill is visible nearby, situated against a backdrop of trees and hills, creating a peaceful retreat.

Home in Canaan

4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

A spacious covered porch features wooden beams and flooring, adorned with three Adirondack chairs facing the scenic surroundings. A ceiling fan provides ventilation under warm natural light, while potted plants add a touch of greenery to the inviting outdoor space.

Home in Chatham

4.7 out of 5 average rating, 10 reviews

Modern Log Chalet - Swimming Pond on 10 acres

BrighamRating, 5 stars2 weeks ago

Can't say enough about how pleasant our stay was! Danielle is a wonderful host - highly communicative and provided us with easy instructions on how to get there, use the house and great places to visit, hike or get groceries. The house is wonderful - very spacious, clean and cozy all at the same time. We loved using the grill and sauna (a great perk!) and the kids loved chasing our dog around the large lawn. We'll definitely return, thank you, Danielle!

Guest favorite

Two black adirondack chairs are positioned on a gravel patio, facing a lush, wooded area filled with trees displaying vibrant autumn foliage. A small wooden table sits between the chairs, creating a serene outdoor space surrounded by nature.

Loft in Austerlitz

4.97 out of 5 average rating, 77 reviews

The Lookout Loft @Moonbeams: stay on 38 acres

StephenRating, 5 stars2 weeks ago

This small studio above a studio was a perfect oasis for a couple. We highly recommend getting the hot tub! Soaking in the tub while listening to the brook down below was one of the highlights of the trip and just an amazing experience overall. Hosts were super responsive and gave us some great recommendations. The weather was less than ideal but we still had an amazing time - very cozy space and a perfect long weekend getaway.

Top guest favorite

A spacious living area features a creamy sectional sofa paired with a minimalist round coffee table. Natural light streams through large windows, casting soft shadows on the light wooden floor. A cozy armchair is complemented by decorative accents, enhancing a calm and inviting vibe.

Cabin in Saugerties

5 out of 5 average rating, 35 reviews

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars3 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

Top guest favorite

A sunlit hallway features a long wooden shelf, lined with an assortment of books. Two windows provide natural light, revealing views of the surrounding greenery. The space opens into the kitchen and dining area, showcasing a blend of rustic and modern design elements.

Home in Old Chatham

4.98 out of 5 average rating, 47 reviews

The Red House

SandyRating, 5 stars2 weeks ago

Leslie's house was wonderful. Comfortable home with lots of space in a peaceful setting. Beautiful views and walking distance to a bird sanctuary with nice trails. We would love to stay here again.

A charming white gate adorned with festive wreaths and red ribbons welcomes guests, framed by snow-covered evergreens. The scene captures the tranquility of winter, with a blanket of fresh snow surrounding the entryway and hints of a property visible in the background.

Guest suite in Spencertown

4.93 out of 5 average rating, 74 reviews

Cozy farmhouse near Chatham, Hudson, Berkshires

ShaynaRating, 5 stars2 months ago

We’ve stayed at Ryan’s place before and always have a great stay. Lots to do in the area, and Ryan is a fantastic host. The place is clean, and they provided coffee, granola, eggs, and yogurt to use during our stay. Would definitely stay again!

Top guest favorite

A modern cabin features a striking facade with large windows, surrounded by colorful trees. An outdoor deck contains multiple seating areas, including lounge chairs and a dining table. A wood-fired hot tub is situated nearby, surrounded by landscaped greenery and gravel pathways.

Cabin in East Nassau

5 out of 5 average rating, 45 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

ElaineRating, 5 stars2 weeks ago

Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!

Show all

Vacation rentals in Spencertown

Top-rated vacation rentals in Spencertown

Vacation rentals for every style

Popular amenities for Spencertown vacation rentals

Other great vacation rentals in Spencertown

Destinations to explore