Places to stay in East Chatham

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Top-rated places to stay in East Chatham

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

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Top guest favorite

Apartment in Canaan

4.99 out of 5 average rating, 161 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.

Top guest favorite

Cabin in Canaan

4.99 out of 5 average rating, 251 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.

Top guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 255 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

Cottage in New Lebanon

4.95 out of 5 average rating, 190 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

Guest favorite

The Chatham House is captured at night, showcasing its distinct architecture with a spacious balcony adorned with lights. An American flag waves gently, while illuminated signs indicate open establishments nearby. Surrounding greenery and decorative elements enhance the inviting façade.

Home in Chatham

4.89 out of 5 average rating, 185 reviews

Chatham Villg Walk to Main. 100% Smoke/Animal Free

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

A wooden porch features structural beams and railings, providing a welcoming entrance to the house. Surrounding greenery includes trees and low-growing plants, creating a natural and shaded ambiance. The exterior is painted in a dark tone, complemented by red doors, enhancing the structure's character.

Home in Chatham

4.89 out of 5 average rating, 171 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. Just 5 minutes away from town center but 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.

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 113 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Top guest favorite

The exterior of the tiny house is presented, featuring a sleek, modern design with large windows allowing natural light. A spacious deck made of wooden planks leads to a seating area with a table and chairs, surrounded by open fields and trees.

Tiny home in Chatham

4.99 out of 5 average rating, 241 reviews

Tiny House, Big Adventure on 70 acres

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. 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

Home in Chatham

4.9 out of 5 average rating, 234 reviews

Pet-friendly. Private. Host leans left. F Trump.

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, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. 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

A spacious wooden deck extends from the cabin, surrounded by trees showcasing autumn foliage. Two chairs are placed on the deck, facing the tranquil wooded landscape, providing a serene spot to enjoy nature.

Cabin in Chatham

4.97 out of 5 average rating, 131 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.

Top guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 408 reviews

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

Guest favorite

Cottage in East Chatham

4.92 out of 5 average rating, 206 reviews

Beautifully Nestled Berkshires Home

Beautifully nestled 19th century colonial house situated on 60 acres of land. Very quiet and peaceful. Great Skiing in the area which include Jiminy Peak and Butternut just 30 minute from the house. 20 minutes from Tanglewood and the Kripalu Center for Yoga and Health. 15 minutes from the charming town of Chatham. 30 minutes from Hudson.