Vacation rentals in Old Chatham

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Top-rated vacation rentals in Old Chatham

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 133 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.

Jan 26 – Feb 2

$135 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 26 – Oct 3

$124 per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 180 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

$133 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.

Dec 2 – 9

$250 per night

Guest favorite

Cabin in Canaan

4.99 out of 5 average rating, 231 reviews

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Oct 4 – 11

$145 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!

Sep 27 – Oct 4

$79 per night

Guest favorite

Home in Ghent

4.96 out of 5 average rating, 213 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Grocery and bar packages are available upon request and can be set-up prior to arrival. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

Feb 26 – Mar 5

$211 per night

Guest favorite

Home in Chatham

4.9 out of 5 average rating, 144 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.

Oct 11 – 18

$102 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.

Nov 26 – Dec 3

$77 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.

Oct 24 – 31

$180 per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 151 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!

Sep 15 – 22

$139 per night

Guest favorite

Guest suite in Nassau

5.0 out of 5 average rating, 222 reviews

Country Two Bedroom Apartment with full breakfast

A ground floor, two bedroom apartment in host's house. Full breakfast provided. Located in New York's scenic Hudson Valley and convenient to Hudson, the Berkshires, the Catskills, Saratoga, Albany, and more. Full kitchen, separate dining room, private covered patio. Access to 23 acres of open and wooded property.

Mar 11 – 18

$113 per night