Vacation rentals in Spencertown

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Top-rated vacation rentals in Spencertown

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Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Oct 17 – 24

G$20,644 GYD per night

Guest favorite

Cabin in Ghent

4.99 out of 5 average rating, 181 reviews

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom, 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features 5-beds, open floor plan, luxury bathrooms, all-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.

Aug 16 – 23

G$78,903 GYD per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 181 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! 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). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Aug 6 – 13

G$32,012 GYD per night

Guest favorite

Cottage in Kinderhook

4.98 out of 5 average rating, 172 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Sep 25 – Oct 2

G$29,829 GYD per night

Guest favorite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

Jan 10 – 17

G$26,204 GYD per night

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 230 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Oct 8 – 15

G$20,286 GYD per night

Guest favorite

Home in Chatham

4.9 out of 5 average rating, 145 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

Feb 4 – 11

G$23,954 GYD per night

Superhost

Home in Ghent

4.9 out of 5 average rating, 258 reviews

Renovated guesthouse on 52 acres!

Come and stay in our beautiful guesthouse in Ghent, upstate NY. Relax and rejuvenate. Hike our private trail in the woods, grill up some food, and chill with a book by the pond... Enjoy the countryside! Go explore cute towns such as Hudson, Chatham and Great Barrington. PLEASE NOTE: My husband and I are both fully vaccinated for Covid-19. And so is our cleaning lady and our caretaker. Please know that we are taking the actions we can, to disinfect the guesthouse in between guests.

Sep 9 – 16

G$48,801 GYD per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 307 reviews

HunnyHAUS: Deluxe TINY*private spa*walk to town

Reserve this thoughtfully curated space just 2.5 hours from NYC or Boston. You'll fall in love with this PRIVATE oasis in a canopy of trees overlooking the creek. Star gaze from your private hot tub (open year-round), sip cocktails around the fire. Walk to dinner OR cook in the well-equipped kitchen/outdoor grill. Immerse yourself in nature while enjoying the convenience of village life. Steps from restaurants, shops, theater, brewery.

Jul 7 – 14

G$54,674 GYD per night

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Dec 23 – 30

G$18,536 GYD per night

Guest favorite

Cabin in Chatham

4.98 out of 5 average rating, 102 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.

May 24 – 31

G$78,412 GYD per night

Guest favorite

Home in Chatham

4.88 out of 5 average rating, 191 reviews

Pet-friendly, Chatham, NY. No neighbors in sight.

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, hammock, glider bench/swing, chairs, table and fire pit. 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.

Nov 21 – 28

G$43,161 GYD per night