Chatham places to stay

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Top-rated places to stay in Chatham

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Chatham

4.89 out of 5 average rating, 168 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

Home in Craryville

4.91 out of 5 average rating, 100 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

Cottage in Kinderhook

4.98 out of 5 average rating, 195 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

Home in Chatham

4.88 out of 5 average rating, 154 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. The center of town is 5 minutes away but the place 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.

Guest favorite

Rental unit in Canaan

4.99 out of 5 average rating, 129 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, 246 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

Tiny home in Chatham

4.99 out of 5 average rating, 206 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, 329 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

Rental unit in Valatie

4.94 out of 5 average rating, 175 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.

Guest favorite

Cabin in Chatham

4.98 out of 5 average rating, 112 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

4.89 out of 5 average rating, 222 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 places to stay

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

Superhost

Home in Old Chatham

4.92 out of 5 average rating, 26 reviews

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

Superhost

Guesthouse in Hillsdale

4.76 out of 5 average rating, 17 reviews

Hudson valley and The Berkshires Cottage

Guest favorite

Cabin in Austerlitz

4.97 out of 5 average rating, 65 reviews

The Pinetop Cabin • Near Berkshires + Tanglewood

Guest favorite

Rental unit in East Chatham

4.96 out of 5 average rating, 90 reviews

Bennett Abode

Guest favorite

Home in Old Chatham

4.97 out of 5 average rating, 32 reviews

The Red House

Guest favorite

Rental unit in Coxsackie

5 out of 5 average rating, 88 reviews

Hudson River Beach House

Guest favorite

Guest suite in Hudson

4.99 out of 5 average rating, 71 reviews

Le Soleil Suite - Fire Pit and Views Near Hudson

Guest favorite

Cottage in Chatham

5 out of 5 average rating, 20 reviews

Guesthouse 505

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Quick stats about vacation rentals in Chatham

Total rentals
10 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.1K 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 places to stay

Top-rated places to stay in Chatham

Home in Chatham

Home in Craryville

Cottage in Kinderhook

Home in Chatham

Rental unit in Canaan

Guest suite in Valatie

Tiny home in Chatham

Tiny home in Chatham

Rental unit in Valatie

Cabin in Chatham

Home in Chatham

Home in Chatham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Chatham places to stay

Stay near Chatham's top sights

Other great vacation rentals in Chatham

Home in Old Chatham

Guesthouse in Hillsdale

Cabin in Austerlitz

Rental unit in East Chatham

Home in Old Chatham

Rental unit in Coxsackie

Guest suite in Hudson

Cottage in Chatham

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