Chatham vacation rentals

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Top-rated vacation rentals in Chatham

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Guest favorite

Home in Chatham

4.89 out of 5 average rating, 174 reviews

Chatham Village Fully Stocked Home 100% Smoke Free

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to police station & Main St pubs/pizza/movies/fine dining hopping 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

Cabin in Ghent

4.99 out of 5 average rating, 225 reviews

Cozy chalet w/ fireplace near Hudson & skiing

5-beds, 3-bedroom, 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.

Guest favorite

Cottage in Kinderhook

4.98 out of 5 average rating, 200 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.

Guest favorite

Rental unit in Canaan

4.99 out of 5 average rating, 143 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 252 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!

Guest favorite

Home in Hudson

4.95 out of 5 average rating, 360 reviews

Rushing Rapids Cottage – a birdwatcher's paradise

Complete renovation with privacy. Rural mill worker's cottage is upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a rural paved road and AHET Rail Trail. Minutes to Hudson and Kinderhook. You may see Carolina Wrens, Cardinals, Chickadees, Woodpeckers, Goldfinches and Hummingbirds. The creek to the front attracts Bald and Golden Eagles, Osprey, Blue Herons, Red Tail Hawks, Ducks and Geese. ABSOLUTELY NO PETS ALLOWED.

Guest favorite

Cottage in Stuyvesant

4.94 out of 5 average rating, 155 reviews

Perfect Cottage On A Hill With A View

A peaceful cottage with views of the Hudson River and Sunsets over the Catskill Mountain Range. Personal, private and all inclusive this little cottage is an incredible place to unwind relax and soak in the beauty of the Hudson Valley. With easy access many local hikes, swimming holes, towns and shopping you’ll find This little cottage to be the perfect place to relax with nature & indulge in all of the luxuries that the Hudson Valley has to offer.

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 213 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). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 347 reviews

Sugar Shack - 300 square feet of pure sweetness.

A very Romantic-Private-Peaceful OASIS yet steps from quintessential Main Street lined with restaurants, brewery, shops, theater. A blissful & sweet retreat only 2.5 hrs from NYC & Boston. This custom space (tiny home+hot tub+she-shed) provides the utmost privacy and is thoughtfully designed with indulgence in mind. Hike, explore town, soak in your private hot tub, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

Guest favorite

Cabin in Chatham

4.97 out of 5 average rating, 116 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.

Guest favorite

Home in Chatham

4.9 out of 5 average rating, 229 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.

Guest favorite

Home in Chatham

4.98 out of 5 average rating, 106 reviews

Hilltop studio apartment on 100 acres near village

Large newly restored studio apartment attached to a single family home nestled in a quiet pastoral setting just outside the Village of Chatham, NY. Your private entrance leads to a bright 20' X 40' room, and includes a full bathroom, kitchen (no cooktop or oven) with a 2nd floor view of the countryside. The host lives full time in the main house.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Chatham's top sights

Chatham Brewing114 locals recommend

Crandell Theatre78 locals recommend

Our Daily Bread Deli66 locals recommend

Blue Plate62 locals recommend

Price Chopper65 locals recommend

The People's Pub54 locals recommend

Other great vacation rentals in Chatham

Guest favorite

Home in Ghent

5 out of 5 average rating, 20 reviews

Hawthorne Valley Barn

Guest favorite

Home in Chatham

4.93 out of 5 average rating, 14 reviews

Cozy Chatham Retreat

Guest favorite

Serviced apartment in Chatham

4.97 out of 5 average rating, 37 reviews

Spacious serviced apartment in Chatham landmark

Guest favorite

Home in Old Chatham

4.97 out of 5 average rating, 34 reviews

The Red House

Guest favorite

Home in Ghent

4.88 out of 5 average rating, 299 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Guest favorite

Cottage in Chatham

4.89 out of 5 average rating, 44 reviews

Cozy Farmhouse Near Hudson, NY

Guest favorite

Cottage in Chatham

5 out of 5 average rating, 24 reviews

Guesthouse 505

Guest favorite

Cottage in Kinderhook

4.96 out of 5 average rating, 82 reviews

Spacious Cottage Retreat on Beautiful 2-Acres

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Quick stats about vacation rentals in Chatham

Total rentals
10 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.3K reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Local attractions
Columbia County Fair Grounds, Chatham Brewing, and Our Daily Bread Deli

Chatham vacation rentals

Top-rated vacation rentals in Chatham

Home in Chatham

Cabin in Ghent

Cottage in Kinderhook

Rental unit in Canaan

Guest suite in Valatie

Home in Hudson

Cottage in Stuyvesant

Tiny home in Chatham

Tiny home in Chatham

Cabin in Chatham

Home in Chatham

Home in Chatham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Chatham vacation rentals

Stay near Chatham's top sights

Other great vacation rentals in Chatham

Home in Ghent

Home in Chatham

Serviced apartment in Chatham

Home in Old Chatham

Home in Ghent

Cottage in Chatham

Cottage in Chatham

Cottage in Kinderhook

Quick stats about vacation rentals in Chatham

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore