Places to stay in East Chatham

Book unique places to stay, houses, and more on Airbnb

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

An outdoor deck area features comfortable seating arrangements with weather-resistant furniture, surrounding a central coffee table. A stone fireplace stands at one end, with lush greenery in view, creating a serene environment for relaxation and outdoor dining.

Guesthouse in Woodstock

5 out of 5 average rating, 378 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO ALL 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE on deck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favorite

A spacious living area features a central brick fireplace surrounded by built-in bookshelves. Light-colored sofas are arranged around a glass coffee table on a patterned rug, with large windows providing natural light and views of the outdoors.

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Guest favorite

A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.

Apartment in Stockbridge

4.96 out of 5 average rating, 104 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

Superhost

A brick fireplace serves as a focal point, with several white candles arranged on the hearth. Natural light filters through a nearby window adorned with sheer curtains, illuminating the seating area with cozy cushions beside a built-in bookshelf.

Apartment in Kingston

4.77 out of 5 average rating, 115 reviews

In the Heart of Kingston

Pet friendly. A comfortable apartment in the heart of midtown Kingston. Enjoy a cup of coffee in the garden, or curl up with a book in the window seat in the living room. This apartment is a great spot to relax from a day of exploring Kingston. You will be close to everything when you stay at this centrally-located place. Note: located near a train; so if you are a light sleeper, it might not be a good fit. Garden area is still in winter mode (until May 15th), so please excuse the mess.

Top guest favorite

A tree with a spiral staircase decorated with string lights is featured, creating a charming morning or evening ambiance. The surrounding garden is lush with various greenery, enhancing the natural setting. Soft illumination from the lights highlights the texture of the tree bark.

Home in Mount Tremper

4.92 out of 5 average rating, 190 reviews

Rippleside Retreat - Stay and Relax

LOCATION, LOCATION! Spacious and quiet creek-front and mountain view home. Near Phoenicia and Woodstock for shopping, browsing art galleries, and fine dining. Plenty of hiking trails, fishing, and tubing in the warmer months, and close to skiing at Belleayre, Hunter, Windham, and Plattekill Mountains for winter enthusiasts. The home is conveniently located near the Emerson Resort and Spa, Foxfire Mountain House, Howland House, Mount Tremper Arts, and Onteora Mountain House wedding venues.

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

Home in Freehold

4.95 out of 5 average rating, 158 reviews

Come and Stay at Our Catskill Hideaway

Follow us at catskill_hideaway Come and Stay at our Catskill Hideaway. We have some of the best places for skiing, snowmobiling, snow tubing, shopping, eating, swimming, hiking, mountain biking, and much more. Within only 30 minutes of this haven.5-Star Super Host for three years. This 900 sq. ft. home is very cozy, with three bedrooms and two bathrooms. This location is perfect when you need a break from the hustle & bustle of life. Relax & enjoy the beautiful Catskill mountains.

Guest favorite

An outdoor deck is shown, featuring wooden flooring and a black railing. Lush green trees and a grassy area create a serene backdrop, while a clear blue sky is visible above. A white chair is positioned on the deck, inviting relaxation.

Condo in Hunter

4.9 out of 5 average rating, 89 reviews

Cozy Slope Side Retreat

Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Creekfront I Hot Tub I Sauna I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB - SAUNA - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Top guest favorite

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Guest favorite

Home in Tannersville

5 out of 5 average rating, 44 reviews

Luxury Custom Home With Hot Tub Minutes From Town

Just minutes from Hunter Mountain, scenic hikes, and breathtaking Catskill views, our custom home is ideally located—only a block from the best restaurants and shopping in town. With high-end amenities, including a chef’s kitchen, heated floors, fireplace, pool table, entertainment system, and an outdoor kitchen with BBQ, pizza oven, fire pit, and hot tub. Perfect for friends and family, just 2.5 hours from Manhattan—your ideal mountain escape!

Top guest favorite

Two wooden Adirondack chairs face a small fire pit, surrounded by a serene wooded area. A picnic table is positioned nearby, with a stack of firewood to the side. The Green River flows gently in the background, framed by vibrant greenery.

Apartment in Williamstown

5 out of 5 average rating, 124 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

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What guests are saying

Mountain View Catskill Escape-2 Mins to Slopes!

4.91 out of 5 average rating, 78 reviews1 week ago

This was such a lovely Airbnb and the hosts were amazing - so responsive and kind. The house had everything me and my family needed during our stay. They even had a pack n play for my baby which I actually forgot to bring! Such a pleasant surprise. The place was spacious and beds were super comfortable. My only critique was the bathtub that no matter how tight you turned it off, it still dripped! We cooked a majority of our meals in the Airbnb because as it turns out, the entire town is closed during spring break! haha only a couple restaurants were open but all and all, great place, great view, great stay! We had a blast playing in the snow, hiking, sitting by the fire, and cooking meals together.

Townhouse in Hunter

What guests are saying

Heart of Catskills:Pond Views,Backyard Dining+BBQ.

4.95 out of 5 average rating, 20 reviews3 days ago

Came back for another lovely stay! This is the perfect location for outdoor activities and still close to our favs like Hudson & Woodstock. House had everything we needed to stay with two young kids and the backyard can’t be beat! Host is fast to reply and accommodating. Would absolutely recommend!

Home in Round Top

What guests are saying

NatureRetreat3BRCabinPrivateTrailToRiver

4.97 out of 5 average rating, 66 reviews4 days ago

Truly a magical stay! A cabin in the woods doesn't get better than this! From the grill to the board games we had everything we needed to disconnect for a bit and tune in with Nature. Tony is very welcoming and hospitable. Beautiful hike to a river out back... book this place!

Cabin in Jewett

What guests are saying

The Serendipity Spot

4.95 out of 5 average rating, 40 reviews2 months ago

Their place was perfect for a couples weekend getaway. It was very clean, convenient, and we loved our stay there. The overall location and the town itself were perfect for our romantic ski weekend plans. Andrew and Susanne were very kind and inviting and were excellent hosts!

Guest suite in Great Barrington

What guests are saying

Creekside Cottage Retreat: Light, Cozy, Getaway

4.92 out of 5 average rating, 24 reviews6 months ago

Cooper’s airbnb was excellent for the price. It was quiet, clean and cozy. Not the most updated home, but again great for the price. Amazing location. Centrally located and had a gorgeous yard and backyard creek. Cooper was very responsive and helpful! Highly suggest for a casual trip (:

Cottage in Saugerties

What guests are saying

King Bed, Wi-Fi, 2m Ski Resort

4.94 out of 5 average rating, 72 reviews1 week ago

Great find! My husband and I were visiting friends in GB and out dog sitting fell through, we searched around and found this great spot and were able to bring our furry friend with us. We are so glad we found this place! It was quiet and our anxious dog settled in so well - it felt like home to all of us.

Apartment in Great Barrington