Title: Chatham Vacation Home Rentals from CA $215: 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

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-07-24&endDate=2026-07-26&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)

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/4eca34ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/34a7dcb3.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)

### 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 $244

CA $436 total

includes taxes & fees

Apr 12 - Apr 13

[](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)

![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/60000000/60000000/59995300/59995220/90-00a818b8.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

(31 reviews)

"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"

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

Olivia C.

CA $164

CA $215 total

includes taxes & fees

Apr 23 - Apr 24

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

![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/17eb3346.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/101000000/100750000/100744600/100744543/cd862c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/e34520e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100750000/100744600/100744543/86ccc561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Catskill Cottage Walk to Downtown & River Views

[](https://www.expedia.ca/Catskill-Hotels-Catskill-Cottage-Walk-To-Downtown-River-Views.h100744543.Hotel-Information)

Catskill

10/10

Exceptional

(20 reviews)

"Great little place to stay at right in downtown!!"

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

Bryan S.

CA $180

CA $307 total

includes taxes & fees

Apr 17 - Apr 18

[](https://www.expedia.ca/Catskill-Hotels-Catskill-Cottage-Walk-To-Downtown-River-Views.h100744543.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)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.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)

### 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 $171

CA $494 total

includes taxes & fees

Apr 6 - Apr 7

[](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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.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

(28 reviews)

"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "

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

maureen k.

CA $286

CA $452 total

includes taxes & fees

Apr 16 - Apr 17

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

![Exterior](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/c945b9f5.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)

### 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

(10 reviews)

"Great place. Exactly like the pictures. "

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

robert a.

CA $223

CA $477 total

includes taxes & fees

Apr 20 - Apr 21

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

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/cc4451e8.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)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/9af2b9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Riverside Berkshires Retreat

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

Great Barrington

9.2/10

Wonderful

(13 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 $267

CA $419 total

includes taxes & fees

Apr 6 - Apr 7

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

![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)

![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)

### 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 $211

CA $544 total

includes taxes & fees

Apr 6 - Apr 7

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

![Exterior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402422/4613bc4e.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)

### 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 $383

CA $665 total

includes taxes & fees

Apr 21 - Apr 22

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

![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/122000000/121090000/121082600/121082559/34317c41.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)

### Artists’ Hideaway in Old Chatham

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

Old Chatham

CA $252

CA $748 total

includes taxes & fees

Apr 11 - Apr 12

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.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 $330

CA $698 total

includes taxes & fees

Apr 8 - Apr 9

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

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.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)

![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 $375

CA $689 total

includes taxes & fees

Apr 5 - Apr 6

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

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/412632db.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)

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

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

Lee

9.8/10

Exceptional

(6 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 $259

CA $647 total

includes taxes & fees

Apr 5 - Apr 6

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

![Private kitchen](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/db1d8490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/db949e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/c79d5486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/127000000/126400000/126398500/126398409/82eca24d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

[](https://www.expedia.ca/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.Hotel-Information)

New Lebanon

CA $146

CA $461 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/New-Lebanon-Hotels-NEW-Spacious-4BR-Ski-Getaway-Minutes-To-Jiminy-Bousquet.h126398409.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)

![Dining](https://images.trvl-media.com/lodging/79000000/78090000/78084300/78084253/4faff5bf.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)

![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)

### 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 $502

CA $1,050 total

includes taxes & fees

Apr 15 - Apr 16

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

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

![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115500000/115491000/115490904/cff06c8f.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 $170

CA $569 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/9bc69856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/6468f916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/c41e9570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/38d4cb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.Hotel-Information)

Stephentown

9.0/10

Wonderful

(2 reviews)

"excellent communication with property manager."

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

Nancy H.

CA $244

CA $783 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122156037.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)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.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)

![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

(35 reviews)

"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"

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

Susan

CA $500

CA $1,011 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/dac46480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/97c48259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/18a5d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/60aae901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hudson Hot Tub & Pet Escape

[](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information)

Stottville

10/10

Exceptional

(2 reviews)

CA $237

CA $434 total

includes taxes & fees

Apr 7 - Apr 8

[](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/53ad91f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/ece4965a_edited_692a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6f64b785_edited_9a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/dcf5df54_edited_d00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Berkshires retreat on mtn resort, SISO

[](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.Hotel-Information)

Hancock

9.0/10

Wonderful

(7 reviews)

"Kind and responsive host."

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

Javier

CA $225

CA $758 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Hancock-Hotels-Comfortable-Berkshires-Retreat-On-Mtn-Resort.h109434975.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

Cottages

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Private vacation homes

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Apartments

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Villas

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Condos

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Houseboats

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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=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CHALET)

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## Top Chatham Hotel Reviews

![Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129_y.jpg)

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

10/10 Excellent

"This little cabin is all you need if you’re looking for a nice getaway in the Catskill mountains."

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

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg)

### Vacation Village in the Berkshires

8/10 Good

"Beds could be more updated"

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

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg)

### Berkshires Untold

4/10 Poor

"this is a MOTEL. nothing indicates, in fact, photos are very misleading. Noisy if you are in front on busy highway. AND, allow pets...when asked for room in back, not facing noise, I almost gagged, ok, I did gag at the smell of furry animals that were guests in that room for sure! Fridge needed defrosting badly (so I did it). Bed lamps glued to table so can't raise up to read in bed! Ok, if you are prepared for a motel!"

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Country Inn & Suites by Radisson, Downtown Albany New York](https://images.trvl-media.com/lodging/112000000/111490000/111484500/111484416/9956a2ad_y.jpg)

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

8/10 Good

"The heater was on pretty high, not a big deal but it was warm in there "

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

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg)

### Hotel On North

10/10 Excellent

"What a lovely room and building. Really enjoyed this hotel. However, the neighborhood outside the hotel was very sketchy and clearly there is an issue with drug addiction in the area. I ate at the restaurant within the hotel and went to and from my car in the gated lot. I enjoyed many other towns in the Berkshires, but Pittsfield was not one of them. Wish this hotel was in a different city, as I would love to stay there again. "

[](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg)

### The Red Lion Inn

10/10 Excellent

"What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again. "

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

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

8/10 Good

"Room temperature was good. Breakfast coukd improve, lack of protein, muffins were not fresh. "

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

"This was a very nice stay. The gentleman that checked us in was friendly, funny, knowledgeable and very welcoming. "

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then"

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

## Find out more about Chatham

## Chatham Vacation Homes information

| Number of reviews | 244                |
| ----------------- | ------------------ |
| Accommodation     | 490 Vacation Homes |
| Lowest Price      | CA $215            |
| Highest Price     | CA $1,050          |

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- [Motels in Niverville ](https://www.expedia.ca/Niverville-Motels.d3000449167-aaMotels.Travel-Guide-Accommodation)
- [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)
- [Hotels with a Pool in Old Chatham ](https://www.expedia.ca/Old-Chatham-Hotels-Hotel-With-Pool.0-0-d6190671-tHotelwithPool.Travel-Guide-Filter-Hotels)
- [Old Chatham Hotels ](https://www.expedia.ca/Old-Chatham-Hotels.d6190671.Travel-Guide-Hotels)
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- [Cheap Hotels in Philmont ](https://www.expedia.ca/Philmont-Hotels-Cheap-Hotels.0-0-d3000351149-tCheapHotels.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)
- [Flights from Nassau ](https://www.expedia.ca/lp/flights/3000449135/flights-from-nassau)
- [Flights from Old Chatham ](https://www.expedia.ca/lp/flights/6190671/flights-from-old-chatham)
- [Flights from Augusta (AGS) to Hudson (HCC) ](https://www.expedia.ca/lp/flights/ags/hcc/augusta-to-hudson)
- [Flights from Bangor (BGR) to Hudson (HCC) ](https://www.expedia.ca/lp/flights/bgr/hcc/bangor-to-hudson)
- [Flights from Cleveland (CLE) to Hudson (HCC) ](https://www.expedia.ca/lp/flights/cle/hcc/cleveland-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)