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A calm lake surrounded by dense evergreen trees and a few deciduous trees with autumn leaves.

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Our top choices for East Chatham holiday homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

A living room with two grey sofas, a wooden coffee table, a painting on the wall, and a lamp.

A white house with a porch, surrounded by a grassy lawn and trees with autumn foliage.

1. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "

Joanna P.

The price is £156

£156

includes taxes & fees

27 Aug - 28 Aug

NEW RENO - Chalet-style farm loft near Tanglewood

A camping setup with a metal chair and a table by a river in a forest.

A forested path with a building in the background.

A living room with a brick wall, a black leather sofa, a patterned armchair, a coffee table, and a ceiling fan.

A living room with two leather sofas, a coffee table, a patterned ottoman, and a lamp on a side table.

2. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "

Jessica V.

The price is £252

£252

includes taxes & fees

20 Sept - 21 Sept

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

A modern building with a wooden deck and a door.

A deck with a table and chairs, a large umbrella, and a hot tub.

A dining area with a wooden table, black wicker chairs, and a white vase. There is a painting on the wall and a ceiling light fixture.

A spacious living room with a large coffee table, two sofas, and a dining area in the background.

3. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"

Terri E.

The price is £431

£431

includes taxes & fees

13 Sept - 14 Sept

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

A spacious living room with a dining area, a kitchen, and a large window.

A gazebo with a stone floor and a grassy area with trees in the background.

A kitchen with white cabinets, a wooden dining table, and a large window.

A living room with a glass coffee table, a sofa, a TV, and a dining area with chairs and a table.

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"

Leslie H.

The price is £176

£176

includes taxes & fees

14 Sept - 15 Sept

1800s Carriage house in Berkshires / Hudson Valley

A white two-story house with a porch, surrounded by trees and a hill.

A cozy living room with a green sofa, a patterned armchair, a wooden coffee table, and a bookshelf.

A dining room with a wooden table and chairs, a fireplace, and a chandelier.

A grassy outdoor area with a seating arrangement.

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley

Canaan

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "

Christine C.

The price is £388

£388

includes taxes & fees

14 Sept - 15 Sept

1789 Shaker Farmhouse in Berkshires/Hudson Valley

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A dining area with a wooden table and chairs, a large wooden cabinet, and a kitchen in the background.

A modern living room with a fireplace, white cabinetry, a large flat-screen TV, and a cozy seating area with patterned cushions.

A wooden deck with a bench and umbrella, a door, and a window.

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

"excellent communication with property manager."

Nancy H.

The price is £406

£406

includes taxes & fees

30 Aug - 31 Aug

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

A wooden deck with a staircase leading to a covered porch area.

A serene lakeside setting with autumn foliage, a white building with multiple windows, and a calm water body.

A gravel pathway leading through a garden with a wooden pergola structure and a lattice fence.

A cozy living room with a sofa, a coffee table, and a TV. There's a dining area with a table and chairs, and a kitchen with a refrigerator and cabinets.

7. All the comforts of home

All the comforts of home

Hudson

9.2 out of 10, Wonderful, (35 reviews)

9.2/10

Wonderful

(35 reviews)

"Great location and super welcoming "

Julie B.

The price is £106

£106

includes taxes & fees

31 Aug - 1 Sept

All the comforts of home

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

A sunlit room with a wooden bench, a cushioned sofa, and a small table.

A kitchen with wooden cabinets, a refrigerator, and a window with curtains.

A dining room with a wooden table, chairs, and a vase of flowers. There is a window with a view of greenery outside.

8. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington

9.6 out of 10, Exceptional, (23 reviews)

9.6/10

Exceptional

(23 reviews)

"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"

Colin E.

The price is £218

£218

includes taxes & fees

24 Sept - 25 Sept

Cozy Riverside Berkshires Retreat

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

A kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a window with a view of trees.

A compact laundry room with a front-loading washer and dryer, a microwave, and a shelf with stacked plates.

A porch with a wooden table and two wicker chairs, a small stool, and a window with blinds.

9. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"

Peter S.

The price is £235

£235

includes taxes & fees

1 Sept - 2 Sept

Sweet Cozy Victorian in Housatonic. Close to everything.

A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

A modern kitchen with white cabinetry, a wooden island, and pendant lighting.

A modern kitchen with a central island, stainless steel refrigerator, and pendant lighting.

A modern living room with a leather sofa, a flat-screen TV, a fireplace, and a kitchen area visible in the background.

10. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub

New Lebanon

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "

Anonymous traveller

The price is £379

£379

includes taxes & fees

9 Sept - 10 Sept

NEW RENO Historic Creamery in Berkshires w/hot tub

A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

A two-story house with a front porch, a small garden with a table and chairs, and a staircase leading to the entrance.

A dining area with a wooden table, chairs, and a rug. There is a kitchen visible in the background.

A living room with a flat-screen TV, a coffee table, two armchairs, a sofa, and a ceiling light fixture.

11. stylish Berkshires Retreat

stylish Berkshires Retreat

Lee

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

The price is £274

£274

includes taxes & fees

9 Sept - 10 Sept

stylish Berkshires Retreat

A group of people seated around a table outdoors with a view of a backyard and houses in the background.

A living room with a leather sofa, a coffee table, a bar area with stools, and a television.

A living room with a fireplace, leather sofa, armchair, and a television mounted on the wall.

A bar area with a long counter, bar stools, a television mounted on the wall, and framed pictures on the wall.

12. Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Hudson’

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We were only there for one night, but we really liked this space - it was clean and the beds were so comfortable! Thanks so much to our host for opening his home to us."

Rachel P.

The price is £248

£248

includes taxes & fees

31 Aug - 1 Sept

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

A modern kitchen with a central island, bar stools, and a window with a view of trees.

A kitchen with a gold faucet, a vase with flowers, and wine glasses on the counter.

A wooden cabin with a curved roof, large windows, and a small porch area.

13. Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."

Lauren C.

The price is £409

£409

includes taxes & fees

8 Sept - 9 Sept

Treat yourself at the stunning June Farms Wellness Huts!

A couple in a hot tub with a natural landscape in the background.

A spacious living room with wooden flooring, a television, a sofa, and a dining area with a table and chairs.

A spacious room with wooden flooring, a black and white bench, a small table with a plant, and a door leading to an outdoor area.

A two-story house with a balcony, surrounded by lush greenery.

14. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Hudson

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "

Jeffrey D.

The price is £530

£530

includes taxes & fees

31 Aug - 1 Sept

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

A modern kitchen with a central island, built-in appliances, and a dining area with a round table.

A modern interior with a dining area, kitchen, and a living space with a view.

A modern kitchen with white cabinets, a wooden dining table, and a ceiling light fixture.

A modern kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a ceiling light fixture.

15. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

Stottville

The price is £555

£555

includes taxes & fees

7 Sept - 8 Sept

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

A wooden deck with a table and chairs, surrounded by a white railing.

A modern kitchen with grey cabinets, a black refrigerator, a microwave, and a dishwasher.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

A residential area with houses, a driveway, and a body of water in the background.

16. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

8.4 out of 10, Very good, (10 reviews)

8.4/10

Very good

(10 reviews)

"Very clean and spacious! We enjoyed our stay with our small pup!"

Ann C.

The price is £396

£396

includes taxes & fees

1 Sept - 2 Sept

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

A staircase with wooden steps and a wall-mounted table with two chairs.

A modern interior with a wooden staircase, a dining area with stools, a sofa, and a kitchen in the background.

A modern kitchen with a central island, wooden beams, and a large window.

17. Home in Great Barrington

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (38 reviews)

9.8/10

Exceptional

(38 reviews)

"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"

HEATHER G.

The price is £299

£299

includes taxes & fees

3 Sept - 4 Sept

Home in Great Barrington

A wooden deck with a wicker sofa, a hammock, and a grill.

A modern kitchen with a central island, wooden dining table with white chairs, and pendant lighting.

A bedroom with a bed, a macrame wall hanging, bedside lamps, and a wooden door.

A modern kitchen with a central island, wooden cabinets, and bar stools.

18. Larkspire I Sleepy Hollow Lake I Beach & Firepit

Larkspire I Sleepy Hollow Lake I Beach & Firepit

Athens

The price is £397

£397

includes taxes & fees

15 Sept - 16 Sept

Larkspire I Sleepy Hollow Lake I Beach & Firepit

A wooden cabin with a door open to a sandy beach, a sign reading "Ditch House," and a view of a lake and forest in the background.

A wooden cabin with a small porch and a bench, situated on a sandy beach with a dog nearby.

A hallway with a brick wall, a wooden door, a red carpet, a coffee maker, and a shelf with a plant and books.

A modern living room with a grey sofa, a round coffee table, and a large window with blinds.

19. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Hudson

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Nice house, decorations well done… communications with host were answered very quickly!"

Brittaney O.

The price is £365

£365

includes taxes & fees

23 Sept - 24 Sept

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

A large white house with black shutters, surrounded by snow-covered trees and a fence.

A sign for The Hancock Village Inn in Berkshire, Massachusetts, with a rustic outdoor setting including a wooden bench, pumpkins, and a corn decoration.

A wooden cabinet with multiple compartments, including glass doors and drawers, likely used for storage.

20. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock

10.0 out of 10, Exceptional, (22 reviews)

10/10

Exceptional

(22 reviews)

"Amazing Inn. Cozy and everything we needed. "

Price F.

The price is £843

£843

includes taxes & fees

9 Sept - 10 Sept

Hancock Village Inn Near Jiminy Peak

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top East Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent

"VERY CLEAN AND LOTS OF FRESH TOWELS"

Emily 2-night trip

Posted 3 hours ago

Country Inn & Suites by Radisson, Downtown Albany New York

The Yankee Inn

10/10 Excellent

"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."

Anne 1-night trip

Posted 3 hours ago

The Yankee Inn

The Red Lion Inn

10/10 Excellent

"The room was very nice, super clean. Sitting on the porch is what we love most. Food was good, drinks a bit pricey..but when you're on vacation it hardly matters. The pool was nice, the hot tub too. A pleasant stay in a historic inn. It's the berkshires so its beautiful"

wayne 2-night trip

Posted 5 hours ago

The Red Lion Inn

Berkshire Mountain Lodge

10/10 Excellent

"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"

David R. 3-night trip

Posted 5 hours ago

Berkshire Mountain Lodge

Hampton Inn & Suites Albany-Downtown

8/10 Good

"Valet service great. Friendly staff. Basic clean rooms. Short walk to Palace Theatre."

Michelle 1-night trip

Posted 6 hours ago

Hampton Inn & Suites Albany-Downtown

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"The experience and the comfort of the stay were appreciated."

George 2-night trip

Posted 7 hours ago

Comfort Inn & Suites East Greenbush - Albany

Albany Plaza Hotel

10/10 Excellent

"I was very happy with my stay!"

Yukiko 1-night trip

Posted 2 days ago

Albany Plaza Hotel

Hilton Albany

10/10 Excellent

"Shuttle was on time and was great to have since the hotel is not close to the airport."

Georgia 1-night trip

Posted 2 days ago

Hilton Albany

Inn at Silver Maple Farm

10/10 Excellent

"Breakfast was fabulous, staff extremely friendly and helpful, and the setting lovely. Mattress too soft for our liking, but otherwise The room very comfortable and well-equipped."

Elizabeth 2-night trip

Posted 2 days ago

Inn at Silver Maple Farm

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews	169
Accommodation	527 Holiday Homes
Lowest Price	£106
Highest Price	£843

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in East Chatham on Expedia.com

Search Holiday Homes in East Chatham

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for East Chatham holiday homes

1. NEW RENO - Chalet-style farm loft near Tanglewood

2. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

3. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

4. 1800s Carriage house in Berkshires / Hudson Valley

5. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

6. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

7. All the comforts of home

8. Cozy Riverside Berkshires Retreat

9. Sweet Cozy Victorian in Housatonic. Close to everything.

10. NEW RENO Historic Creamery in Berkshires w/hot tub

11. stylish Berkshires Retreat

12. Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

13. Treat yourself at the stunning June Farms Wellness Huts!

14. Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

15. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

16. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

17. Home in Great Barrington

18. Larkspire I Sleepy Hollow Lake I Beach & Firepit

19. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

20. Hancock Village Inn Near Jiminy Peak

Find holiday rentals that suit your style

Top East Chatham Hotel Reviews

Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about East Chatham

East Chatham Holiday Homes information

Explore a world of travel with Expedia