Vacation rentals in North Chatham

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Top-rated vacation rentals in North Chatham

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

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 134 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar 12 – 19

ﺩ.ﺇ577 per night

Guest favorite

Yurt in Pattersonville

4.99 out of 5 average rating, 773 reviews

Mariaville Goat Farm Yurt

A peaceful, charming, 20’ yurt in the woods on our small, off-the-grid goat farm! If you are looking to get away from it all (and still be close to SO much) - this is the place for you! Enjoy a nap in the hammock, s’mores around a campfire, a great night’s sleep under the stars, a country breakfast delivered to your door - and goats! Take a walk in the woods...enjoy the unique landscaping...try goat yoga! Or, experience some of the area’s AMAZING food, beverages, shopping, and attractions!

Feb 28 – Mar 7

ﺩ.ﺇ553 per night

Guest favorite

Cottage in Kinderhook

4.98 out of 5 average rating, 173 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.

Jun 10 – 17

ﺩ.ﺇ536 per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 183 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.

Oct 15 – 22

ﺩ.ﺇ575 per night

Guest favorite

Cottage in Valatie

4.99 out of 5 average rating, 127 reviews

Kinderhook Lake Retreat-private+kayaks/sup+swim+ac

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying wildlife -Grab a kayak or paddleboard and explore the lake -Catch the sunset, then take a scenic walk on the Electric Trail -End the day sharing stories around the starlit firepit Close to restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Oct 30 – Nov 6

ﺩ.ﺇ1,186 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!

Aug 29 – Sep 5

ﺩ.ﺇ403 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.

Mar 12 – 19

ﺩ.ﺇ430 per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Sep 7 – 14

ﺩ.ﺇ440 per night

Guest favorite

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.

Feb 23 – Mar 2

ﺩ.ﺇ335 per night

Guest favorite

Tiny home in Nassau

4.97 out of 5 average rating, 132 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays welcome!! *** IMPORTANT *** Our pictures show that screens can be closed around the porch - we had to take these down as pets were tough on these. Pets LOVE the property, so it was important for us to remain pet friendly. The screens are no longer on the tiny house. Stay in our clean, sweet, one-of-a-kind tiny home. The home is waterfront with your own private peninsula with a sandy area to walk into the water.

Jan 26 – Feb 2

ﺩ.ﺇ720 per night

Guest favorite

Apartment in Valatie

4.94 out of 5 average rating, 164 reviews

Holland House: Modern Rustic Guest Apartment

Thoughtfully designed two-bedroom apartment located above a former millinery shop built in 1880. Beautiful natural light. Mix of vintage and modern amenities, including two guest bedrooms, full kitchen and bath, high speed wifi, in-unit laundry and work desks. Private tree-shaded back porch overlooking Kinderhook Creek and Pachaquack Preserve. 20 minutes to Hudson. 30 minutes to Albany, the Berkshires and the Catskills.

Jan 20 – 27

ﺩ.ﺇ530 per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 153 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Aug 29 – Sep 5

ﺩ.ﺇ600 per night