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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 cozy living room with a sofa, a fireplace, and large windows.

A rustic wooden building with a metal roof, surrounded by lush greenery and a large tree.

A bedroom with a large bed, a chair, a floor lamp, and a painting.

A spacious living room with wooden beams, large windows, a chandelier, and a fireplace.

1. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna

East Chatham

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Peaceful weekend spot"

Michael T.

The price is €624

€624

includes taxes & fees

27 Oct - 28 Oct

Luxury Barn Near Hudson With New Private Sauna

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

A compact kitchen with a dining table and chairs, a microwave, and a refrigerator.

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

2. 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 €192

€192

includes taxes & fees

27 Oct - 28 Oct

NEW RENO - Chalet-style farm loft near Tanglewood

A spacious living room with a dining area, a kitchen, 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.

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

A bedroom with a bed, two bedside tables, a window, a skylight, and a door leading outside.

3. 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 €204

€204

includes taxes & fees

5 Nov - 6 Nov

1800s Carriage house in Berkshires / Hudson Valley

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.

4. 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, (16 reviews)

10/10

Exceptional

(16 reviews)

"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"

Jess S.

The price is €304

€304

includes taxes & fees

27 Oct - 28 Oct

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

A modern building with a wooden deck and a door.

A living room with a brown sofa, a wooden dining table, and a kitchen area in the background.

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

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

5. 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 €621

€621

includes taxes & fees

27 Oct - 28 Oct

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

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

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

A grassy outdoor area with a seating arrangement.

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

6. 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 €394

€394

includes taxes & fees

27 Oct - 28 Oct

1789 Shaker Farmhouse in Berkshires/Hudson Valley

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 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.

A kitchen with wooden cabinets, a built-in microwave, a coffee maker, and a sink.

7. All the comforts of home

All the comforts of home

Hudson

9.2 out of 10, Wonderful, (38 reviews)

9.2/10

Wonderful

(38 reviews)

"No frills, very clean and peaceful, beautiful setting"

Lori M.

The price is €130

€130

includes taxes & fees

1 Nov - 2 Nov

All the comforts of home

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 spacious kitchen with a large island, built-in appliances, and a laundry area.

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

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

Stephentown

9.2 out of 10, Wonderful, (10 reviews)

9.2/10

Wonderful

(10 reviews)

"A lovely house! Very convenient for a Tanglewood weekend."

Robert B.

The price is €527

€527

includes taxes & fees

27 Oct - 28 Oct

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

A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

A modern kitchen with built-in appliances, wooden cabinets, and a herringbone floor pattern.

A bedroom with a bed, bedside lamp, and a window with curtains.

9. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!

Richmond

The price is €627

€627

includes taxes & fees

2 Nov - 3 Nov

Ellie’s Overlook, best view in the Berkshires!

A dining area with a wooden table, chairs, and a ceiling fan.

A staircase with a wooden handrail and a white wall with a light switch.

A hallway leading to a bedroom with a dresser and a mirror on the wall.

A two-story house with a wrap-around porch, a fenced yard, and a driveway leading to the house.

10. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires

Great Barrington

9.6 out of 10, Exceptional, (29 reviews)

9.6/10

Exceptional

(29 reviews)

"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

Kelly B.

The price is €254

€254

includes taxes & fees

27 Oct - 28 Oct

Leaf-Peeper Paradise in the Berkshires

A dining area with a wooden table, black chairs, and a vase with green plants.

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

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

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

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

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."

Eric H.

The price is €309

€309

includes taxes & fees

27 Oct - 28 Oct

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 spacious living area with a wooden dining table, a black leather sofa, and a piano.

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

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

12. 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, (8 reviews)

10/10

Exceptional

(8 reviews)

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

Anonymous traveller

The price is €512

€512

includes taxes & fees

27 Oct - 28 Oct

NEW RENO Historic Creamery in Berkshires w/hot tub

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.

A green house with a porch, surrounded by a garden with various plants and flowers.

A house with a covered porch and a well-maintained garden.

13. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 reviews)

"We had a wonderful time, we’d be happy to come back again "

Ofer C.

The price is €576

€576

includes taxes & fees

1 Nov - 2 Nov

Secluded Family Home in Serene Stockbridge Woods

A wooden deck with two Adirondack chairs and a railing, surrounded by trees with autumn foliage.

A two-story house with a front porch, a small garden with autumn leaves, and a clear blue sky.

A kitchen with a central island, a built-in sink, and a ceiling fan.

14. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8 out of 10, Excellent, (12 reviews)

8.8/10

Excellent

(12 reviews)

"Host was proactive in communication and answer each and every question."

Amit

The price is €484

€484

includes taxes & fees

27 Oct - 28 Oct

Comfortable Berkshires retreat on mtn resort, SISO

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

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

A spacious living area with a wooden floor, a sofa, a coffee table, and a TV.

15. 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, (12 reviews)

10/10

Exceptional

(12 reviews)

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

Jeffrey D.

The price is €514

€514

includes taxes & fees

1 Nov - 2 Nov

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

A kitchen with white cabinets, a wooden countertop, and a woven basket.

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 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.

16. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

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 €462

€462

includes taxes & fees

24 Nov - 25 Nov

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

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

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

A modern bedroom with a large bed, a flat-screen TV on a tripod stand, a bedside table with a lamp, and several potted plants.

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

17. 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 €480

€480

includes taxes & fees

3 Nov - 4 Nov

Treat yourself at the stunning June Farms Wellness Huts!

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

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

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.

18. Home in Great Barrington

Home in Great Barrington

Great Barrington

9.8 out of 10, Exceptional, (40 reviews)

9.8/10

Exceptional

(40 reviews)

"Wonderful property and host very responsive."

Janet G.

The price is €322

€322

includes taxes & fees

27 Oct - 28 Oct

Home in Great Barrington

A modern living room with a sofa, armchair, coffee table, and TV.

A kitchen with white brick backsplash, stainless steel appliances, wooden cabinets, and a wooden island.

A two-story residential house with a front porch, a small garden, and a tree with autumn leaves.

A living room with a sofa, armchair, coffee table, and a staircase leading to another room.

19. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups

Lee

9.6 out of 10, Exceptional, (4 reviews)

9.6/10

Exceptional

(4 reviews)

"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."

neil s.

The price is €527

€527

includes taxes & fees

1 Nov - 2 Nov

Spacious Central Berkshires Home for Groups

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

A house with a front porch, steps, and a small garden with pink flowers.

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

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

20. Larkspire l Catskills Fall Foliage Lake House

Larkspire l Catskills Fall Foliage Lake House

Athens

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Lovely home with reasonable accessibility. Host was very responsive. Clean and quiet. Beautiful scenery."

Kellie H.

The price is €491

€491

includes taxes & fees

27 Oct - 28 Oct

Larkspire l Catskills Fall Foliage Lake House

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

Quality Inn Great Barrington

10/10 Excellent

"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"

Patricia 2-night trip

Posted 1 hour ago

Quality Inn Great Barrington

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Excellent accommodations! Our room was very clean and comfortable. We appreciated the well lit parking lot, quality breakfast foods, and friendly staff. Thank you!"

Nancy 2-night trip

Posted 3 hours ago

Comfort Inn & Suites East Greenbush - Albany

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

10/10 Excellent

"Really excellent spot for families. Loved having a townhouse to spread out and good kitchenette. Amenities were great and helped get little kids energy out."

Karen 3-night trip

Posted 4 hours ago

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Hotel On North

10/10 Excellent

"Can't wait to go back!"

Mary Ellen 1-night trip

Posted 4 hours ago

Hotel On North

Berkshires Untold

10/10 Excellent

"The hotel is super special and cool interior. The stuff is unbelievable and attentive- specially Sarah and Aurora. Sarah is the light of the place, cares about giving you the best experience. Thank you for a special anniversary"

Shiran 1-night trip

Posted 4 hours ago

Berkshires Untold

Vacation Village in the Berkshires

10/10 Excellent

"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"

Angelina 7-night trip

Posted 5 hours ago

Vacation Village in the Berkshires

Berkshire Mountain Lodge

10/10 Excellent

"Beautiful setting. Spacious room. Even the machine-dispensed coffee was good. Five stars."

Anonymous traveller 1-night trip

Posted 7 hours ago

Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"all good"

Vicki 1-night trip

Posted 1 day ago

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hilton Albany

8/10 Good

"Pretty lobby helpful staff and parking was convenient"

Doris 1-night trip

Posted 3 days ago

Hilton Albany

Find out more about East Chatham

East Chatham Holiday Homes information

Number of reviews	196
Accommodation	484 Holiday Homes
Lowest Price	€130
Highest Price	€627

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. Luxury Barn Near Hudson With New Private Sauna

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

3. 1800s Carriage house in Berkshires / Hudson Valley

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

5. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

6. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

7. All the comforts of home

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

9. Ellie’s Overlook, best view in the Berkshires!

10. Leaf-Peeper Paradise in the Berkshires

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

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

13. Secluded Family Home in Serene Stockbridge Woods

14. Comfortable Berkshires retreat on mtn resort, SISO

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

16. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

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

18. Home in Great Barrington

19. Spacious Central Berkshires Home for Groups

20. Larkspire l Catskills Fall Foliage Lake House

Find holiday rentals that suit your style

Top East Chatham Hotel Reviews

Quality Inn Great Barrington

Find out more about East Chatham

East Chatham Holiday Homes information