Title: Chatham Vacation Home Rentals from CA $193: Search Top Private Vacation Homes for Rent | Expedia.ca

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![Tracy Memorial Village Hall, Chatham, New York](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6046736/7198abd1-0904-483a-a024-c143d8de9574.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chatham vacation homes

![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/dc6494b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/fa10adc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/47a45e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/b7d8032f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Renovated house. Built in 1890s. No neighbors in sight.

[](https://www.expedia.ca/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information)

Chatham

8.0/10

Very good

(1 review)

"Mark was very communicative and helpful, answering all questions quickly and accurately"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jim S.

CA $239

CA $428 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Chatham-Hotels-Renovated-House-Built-In-1890s-No-Neighbors-In-Sight.h124466418.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-950a0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All the comforts of home

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

Hudson

9.2/10

Wonderful

(29 reviews)

"Good for a quick overnight - host was very accommodating when we needed an early check-in."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Katie B.

CA $145

CA $193 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3-bedroom house in beautiful Berkshires, close to amenities!

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

Pittsfield

CA $245

CA $416 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, electric kettle](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/52345b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/055ed8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Ski Getaway in the Berkshires

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

Great Barrington

9.0/10

Wonderful

(11 reviews)

"Close to a great bakery and near to a farm market and shopping mall. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cristine C.

CA $277

CA $430 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/61c037e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/fe54d0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/809aa3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/4613bc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treat yourself at the stunning June Farms Wellness Huts!

[](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information)

West Sand Lake

10/10

Exceptional

(8 reviews)

"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SteveS

CA $340

CA $613 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402422.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/d16bb4cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c363e795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/0afecb87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c945b9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Luxurious Cabin, Catskills - The Tiny Nook

[](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information)

Catskill

10/10

Exceptional

(8 reviews)

"Great place. Exactly like the pictures. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

robert a.

CA $219

CA $471 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Catskill-Hotels-The-Tiny-Nook-Escape-The-City-Life-Relaxing-Getaway-Tucked-In-Catskills.h103819908.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/6b5af50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/00cc85e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

New Lebanon

9.4/10

Exceptional

(26 reviews)

"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul S.

CA $148

CA $461 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

Great Barrington

9.8/10

Exceptional

(27 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cameron M.

CA $220

CA $367 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b86b4635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk into town, soak up sun on enclosed porch & steps away from nature trails!

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

Stockbridge

10/10

Exceptional

(34 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cathy c.

CA $409

CA $889 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

Pittsfield

7.8/10

Good

(7 reviews)

"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Liz V.

CA $368

CA $677 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/w1419h960x21y0-4ecf9f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/68e2333c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/768d59cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/4fb2bcba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artists’ Hideaway in Old Chatham

[](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information)

Old Chatham

CA $221

CA $699 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/f0ba5959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/1df26d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/6d1211ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/fbef3554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Berkshires Home Near Tanglewood, Trails & Wineries

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

Lebanon Springs

9.0/10

Wonderful

(21 reviews)

"Comfy beds, clean, great big deck with a view. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Corinne T.

CA $190

CA $513 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/New-Lebanon-Hotels-Historic-Berkshires-Home-Near-Tanglewood.h84357520.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/f9e412ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/e73723b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/a09a85d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/f86b5b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

[](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.Hotel-Information)

Hudson

9.8/10

Exceptional

(30 reviews)

"The home was as described. Exceptional. It was immaculate and well stocked."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

judy h.

CA $828

CA $1,501 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/fbe651db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/d106f31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/1d777bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/afeec342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Catskill Stay w/ Deck & Fire Pit

[](https://www.expedia.ca/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information)

Catskill

8.8/10

Excellent

(3 reviews)

"we had a great stay at this house with a group of friends - rooms were comfortable and kitchen had a lot of things we needed for meals. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

raquel p.

CA $178

CA $574 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Catskill-Hotels-Catskill-Stay-W-Deck-Fire-Pit.h115490904.Hotel-Information)

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/4d94597a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/dc9a1bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

Great Barrington

10/10

Exceptional

(3 reviews)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roberta

CA $774

CA $1,814 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/2802a7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/f0716890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/e715a827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108910000/108909000/108908975/58aa3713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Barn Retreat — All-Season Escape Awaits!

[](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information)

East Chatham

10/10

Exceptional

(2 reviews)

"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Timothy S.

CA $458

CA $855 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/East-Chatham-Hotels-Spectacular-Barn-With-1-Bedroom-1-Loft.h108908975.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/ab946d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/4ce0af29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/8f9296e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

Sheffield

10/10

Exceptional

(42 reviews)

"The property was centrally located for skiing, and was a comfortable stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly R.

CA $324

CA $691 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/b3db0757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/707c656a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/3fbdaaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/w1440h1897x0y5-29f33d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tao Estate in Catskills : Close to Hiking & Nature & Pet Friendly

[](https://www.expedia.ca/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information)

CATSKILL

9.4/10

Exceptional

(3 reviews)

"Lovely short weekend in the countryside. Calm zen retreat surrounded by nature and animals."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

sarah j.

CA $493

CA $1,030 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Catskill-Hotels-Tao-Estate.h78084253.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/3bd0d6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/6339dfc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/c34ecca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/8b16599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

Housatonic

10/10

Exceptional

(3 reviews)

"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl F.

CA $185

CA $365 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/cd1323be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/621adf1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lenox Retreat - Minutes to Tanglewood!

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

Lee

9.6/10

Exceptional

(4 reviews)

"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paulo I.

CA $246

CA $627 total

includes taxes & fees

Feb 25 - Feb 26

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

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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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CABIN)

Aparthotels

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Cottages

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CHALET)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=HOUSE_BOAT)

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## Top Chatham Hotel Reviews

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Excellent experience "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Yes it was clean as usual."

[](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Country Inn & Suites by Radisson, Downtown Albany New York](https://images.trvl-media.com/lodging/112000000/111490000/111484500/111484416/25b753d6_y.jpg)

### Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent

"Great clean hotel in perfect location "

[](https://expedia.ca/Albany-Hotels-Country-Inn-Suites-By-Radisson.h111484416.Hotel-Information)

![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"Clean, breakfast was a nice option before heading to Butternut mountain nearby "

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Pocketbook Hotel and Bath](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/w4500h2996x0y0-b2a7729b_y.jpg)

### Pocketbook Hotel and Bath

10/10 Excellent

"Beautiful property and rooms great bar and restaurant "

[](https://expedia.ca/Hudson-Hotels-Pocketbook-Hotel-And-Bath.h117877797.Hotel-Information)

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

### Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Absolutely amazing! The place was wonderful and so peaceful! "

[](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.Hotel-Information)

![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg)

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"The room was fresh, recent renovation was done with attention to detail. Breakfast was great. The only thing I can say bad is the coffee was awful"

[](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Yes great stay"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

## Find out more about Chatham

## Chatham Vacation Homes information

| Number of reviews | 240                |
| ----------------- | ------------------ |
| Accommodation     | 490 Vacation Homes |
| Lowest Price      | CA $193            |
| Highest Price     | CA $1,814          |

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- [Villas in Niverville ](https://www.expedia.ca/Niverville-Villas.d3000449167-aaVillas.Travel-Guide-Accommodation)
- [B&B in Old Chatham ](https://www.expedia.ca/Old-Chatham-Bed-And-Breakfast.d6190671-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Historic Hotels in Old Chatham ](https://www.expedia.ca/Old-Chatham-Hotels-Historic-Hotel.0-0-d6190671-tHistoricHotel.Travel-Guide-Filter-Hotels)
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- [Stuyvesant Falls Hotels ](https://www.expedia.ca/Stuyvesant-Falls-Hotels.d3000351295.Travel-Guide-Hotels)
- [Aparthotels in Valatie ](https://www.expedia.ca/Valatie-Apart-Hotels.d183726-aaApartHotels.Travel-Guide-Accommodation)
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- [Resorts in Valatie ](https://www.expedia.ca/Valatie-Resort-Hotels.d183726-aaResortHotels.Travel-Guide-Accommodation)
- [West Lebanon Hotels ](https://www.expedia.ca/West-Lebanon-Hotels.d553248635975867288.Travel-Guide-Hotels)

- [Flights to Nassau ](https://www.expedia.ca/Cheap-Flights-To-Nassau.d3000449135.Travel-Guide-Flights)
- [Flights to Niverville ](https://www.expedia.ca/Cheap-Flights-To-Niverville.d3000449167.Travel-Guide-Flights)
- [Flights to Old Chatham ](https://www.expedia.ca/Cheap-Flights-To-Old-Chatham.d6190671.Travel-Guide-Flights)
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- [Flights from Augusta (AGS) to Hudson (HCC) ](https://www.expedia.ca/lp/flights/ags/hcc/augusta-to-hudson)
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- [Flights from Milwaukee (MKE) to Hudson (HCC) ](https://www.expedia.ca/lp/flights/mke/hcc/milwaukee-to-hudson)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Coxsackie Vacations ](https://www.expedia.ca/Coxsackie.d183657.Destination-Travel-Guides)
- [Visit Kinderhook ](https://www.expedia.ca/Kinderhook.dx121767)
- [Visit Malden Bridge ](https://www.expedia.ca/Malden-Bridge.dx553248635975847470)
- [Nassau Vacations ](https://www.expedia.ca/Nassau.d3000449135.Destination-Travel-Guides)
- [Visit Niverville ](https://www.expedia.ca/Niverville.dx3000449167)
- [Shaker Museum and Library ](https://www.expedia.ca/Shaker-Museum-And-Library-Old-Chatham.d6087137.Vacation-Attraction)
- [Visit Stottville ](https://www.expedia.ca/Stottville.dx3000351293)

- [Car rental Coxsackie ](https://www.expedia.ca/Car-Rentals-In-Coxsackie.d183657.Car-Rental-Guide)

- [Book Vacation Homes in Chatham on Expedia.com ](https://www.expedia.com/Chatham-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation)