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

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 185 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Top guest favorite

An open studio space reveals a kitchenette with modern appliances, including a refrigerator and microwave. A wooden bar with stools is positioned next to a soft seating area. Natural light fills the room through a window, highlighting the rustic wooden beams above.

Cabin in Canaan

4.99 out of 5 average rating, 253 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.

Guest favorite

Cottage in New Lebanon

4.95 out of 5 average rating, 193 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, 187 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, 115 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

Large windows frame a view of vibrant autumn foliage, with shades of green and gold visible in the trees outside. Two stylish chairs are positioned in front of the windows, inviting relaxation while enjoying the scenic landscape.

Bungalow in Cairo

4.99 out of 5 average rating, 438 reviews

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 220 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 just relax out on the balcony and take in the views.

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, 244 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

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

Three decorative ceramic figures are positioned on a countertop, their colorful designs creating a cheerful focal point. Two white mugs are visible nearby, alongside a white utensil holder that contains various kitchen tools. Natural light filters through a window, enhancing the vibrant hues of the figures.

Tiny home in Chatham

4.99 out of 5 average rating, 415 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.

Top guest favorite

A green, spacious yard features two lounge chairs positioned near a fire pit, surrounded by lush grass and vibrant flowering plants. The farmhouse stands in the background, complemented by a rustic barn and mature trees enhancing the natural setting.

Loft in East Nassau

4.99 out of 5 average rating, 181 reviews

Dog Friendly Farm

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!

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Popular amenities for East Chatham places to stay

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Wifi

Other great vacation rentals in East Chatham

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A view of an open living space features a black fireplace and a round dining table. Light wood flooring extends towards a hallway that leads to various rooms. A colorful wall art piece adds a pop of interest, while a plant on the table introduces a touch of greenery.

Home in Chatham

5 out of 5 average rating, 3 reviews

Chatham Farmhouse Hudson Valley

NazariyRating, 5 stars5 months ago

We had an amazing weekend stay at Micah’s place! The home was absolutely stunning—super clean, beautifully furnished, and stocked with everything you could possibly need. The kitchen was fully equipped with all the appliances, making it easy to cook and enjoy meals. The highlight was the TV room, which had incredible sound quality and made for a perfect spot to relax. The home was also very child-friendly, which made our stay even more enjoyable. Overall, a fantastic experience! Highly recommend this place.

Top guest favorite

A wooden deck is surrounded by lush greenery, overlooking a serene natural landscape. Outdoor seating is provided, featuring a coffee table and comfortable chairs. A grill is visible nearby, situated against a backdrop of trees and hills, creating a peaceful retreat.

Home in Canaan

4.96 out of 5 average rating, 55 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

BethRating, 5 stars3 days ago

We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

Top guest favorite

Cottage in Nassau

4.97 out of 5 average rating, 32 reviews

Hook, Wine and Sinker!

CaylorRating, 5 stars1 week ago

Such a nice, quiet, cozy cabin. Truly does not feel like a cabin. The inside is modern and very clean. Surprisingly spacious! Layout is great. The back porch was the best part. We stayed during a rainy weekend, but sitting on the porch over looking the lake to the sound of the rain was beyond peaceful. Truly a hidden gem. I would stay here again and again! HIGHLY RECOMMEND!!

Top guest favorite

A serene outdoor space is presented, featuring two wooden chairs positioned around a fire pit surrounded by gravel. A rustic wooden structure holds firewood nearby, while trees provide a natural canopy overhead, creating a secluded area for relaxation.

Camper/RV in East Nassau

5 out of 5 average rating, 31 reviews

The Hawk's Nest

ArsalanRating, 5 stars5 days ago

We had best time there! awesome host ! She was really kind in entire trip, we were there with our baby and she gave him toys & books ❤️ Everything was perfect and safe , Thanks to her

Guest favorite

A spacious outdoor deck features two black Adirondack chairs positioned around a small table. The rustic wooden cabin exterior is made of vertical timber planks, and large glass doors provide views of the surrounding greenery under a partly cloudy sky.

Cabin in Austerlitz

4.97 out of 5 average rating, 72 reviews

Pinetop Cabin • Near Berkshires + Hudson Valley

MelissaRating, 5 stars5 months ago

We loved our stay in Jeremy and Danielle’s cabin. It was warm and cozy and rustic yet modern. The place was in pristine condition, and we felt immediately at home upon entering. We will definitely rent it again the next time we are in the area. :-)

Top guest favorite

Cabin in Saugerties

5 out of 5 average rating, 38 reviews

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars1 week ago

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

Guest favorite

The living area features a spacious sectional sofa centered around a dark coffee table. A spiral staircase leads to an upper loft, while large windows allow natural light to brighten the room. Warm wooden beams and a pellet stove add to the inviting ambiance.

Cottage in Old Chatham

4.9 out of 5 average rating, 77 reviews

Charming upstate cottage close to Berkshires

ChristinaRating, 5 stars1 month ago

Beautiful Place to Stay, Very Peaceful, and Works Great For Us to Visit With Family in the Area. It's Our 2nd Time Staying Here With Annika, and Would Love to Again Because It's Absolutely Perfect!! ❤️

Top guest favorite

A serene river flows over rocky outcroppings, creating gentle rapids. Lush green trees frame the scene, with some rocks partially covered in moss. The movement of water contrasts with the stillness of the surroundings, providing a tranquil atmosphere in nature.

Apartment in Nassau

4.92 out of 5 average rating, 92 reviews

A Haven of Rest Beautiful Historic Tranquil Suite

ChrysRating, 5 stars4 months ago

Melody's apartment was the perfect base for our visit to Nassau and the Albany area. Comfortable, clean, warm, centrally located, quiet and peaceful - it had everything we could possibly need for our stay. Our dogs loved it too! Highly recommended if you are visiting this area or just passing through.

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Places to stay in East Chatham

Top-rated places to stay in East Chatham

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