Title: Chatham Vacation Home Rentals from CA $192: 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

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-06-05&endDate=2026-06-07&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)

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

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/7be72235.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)

### 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

CA $237

CA $424 total

includes taxes & fees

Feb 16 - Feb 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102020000/102018300/102018223/399488d1.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 $183

CA $362 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Housatonic-Hotels-Sweet-Cozy-Victorian-In-Housatonic-Close-To-Everything.h102018223.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/100000000/99250000/99243600/99243554/43b40eb2.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 $146

CA $455 total

includes taxes & fees

Feb 12 - Feb 13

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-b25e9082.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)

### 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 $144

CA $192 total

includes taxes & fees

Feb 12 - Feb 13

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

![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/c41e9570.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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122160000/122156100/122156037/4be6f104.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

8.0/10

Very good

(1 review)

"excellent communication with property manager."

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

Nancy H.

CA $237

CA $764 total

includes taxes & fees

Feb 21 - Feb 22

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

![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.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)

### 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 $244

CA $621 total

includes taxes & fees

Feb 12 - Feb 13

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

![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103820000/103819908/fee8af1c.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 $217

CA $467 total

includes taxes & fees

Feb 24 - Feb 25

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

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.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 $211

CA $357 total

includes taxes & fees

Feb 23 - Feb 24

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84360000/84357600/84357520/23a17279.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 $209

CA $531 total

includes taxes & fees

Mar 2 - Mar 3

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

![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)

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

### 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

9.2/10

Wonderful

(9 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 $274

CA $400 total

includes taxes & fees

Feb 12 - Feb 13

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

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

### 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 $273

CA $690 total

includes taxes & fees

Feb 12 - Feb 13

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

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/60aae901.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)

### Hudson Hot Tub & Pet Escape

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

Stottville

CA $259

CA $455 total

includes taxes & fees

Feb 17 - Feb 18

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

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402469/2b53a089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402469/14b24ed1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402469/739331ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/94000000/93410000/93402500/93402469/a3cc3167.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.h93402469.Hotel-Information)

West Sand Lake

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."

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

Lauren C.

CA $337

CA $687 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Treat-Yourself-At-The-Stunning-June-Farms-Wellness-Huts.h93402469.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)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/4fb2bcba.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)

### Artists’ Hideaway in Old Chatham

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

Old Chatham

CA $236

CA $716 total

includes taxes & fees

Feb 24 - Feb 25

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

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.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)

![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.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 $251

CA $423 total

includes taxes & fees

Feb 23 - Feb 24

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

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/2158de3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/8ed29c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/78c36899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122120000/122118500/122118449/69de4eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clean Family Retreat for8, 3BR with Fast Wi-Fi,nice Backyard & Plenty of Parking

[](https://www.expedia.ca/Albany-Hotels-3-Bedroom-House-In-Beautiful-Albany-With-AC.h122118449.Hotel-Information)

Albany

8.0/10

Very good

(1 review)

"Overall nice stay "

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

Anonymous traveller

CA $258

CA $398 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Albany-Hotels-3-Bedroom-House-In-Beautiful-Albany-With-AC.h122118449.Hotel-Information)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/1bcf2f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/d712468a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

Great Barrington

9.4/10

Exceptional

(26 reviews)

"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "

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

Deb W.

CA $386

CA $710 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.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)

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

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.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

(33 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 $405

CA $881 total

includes taxes & fees

Feb 16 - Feb 17

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

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/77b3a9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/a0cefac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/2d6b60e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/c53563b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Hudson-Hotels-Blue-Heron-House-3BR-Creekside-Retreat-With-Hot-Tub.h120277085.Hotel-Information)

Hudson

10/10

Exceptional

(3 reviews)

"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "

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

Kim W.

CA $393

CA $821 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Hudson-Hotels-Blue-Heron-House-3BR-Creekside-Retreat-With-Hot-Tub.h120277085.Hotel-Information)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/4f2c31bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/6873f6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/b9e06e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120050000/120045500/120045407/w1424h960x16y0-bffb2a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy. Clean. Free bagel shop. 3 Fireplaces.

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.Hotel-Information)

Great Barrington

10/10

Exceptional

(1 review)

"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"

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

Mary R.

CA $461

CA $793 total

includes taxes & fees

Feb 12 - Feb 13

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop-3-Fireplaces.h120045407.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

Aparthotels

[](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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APART_HOTEL)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN)

Cottages

[](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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VILLA)

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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&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=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=HOUSE_BOAT)

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## Top Chatham Hotel Reviews

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg)

### Hotel On North

10/10 Excellent

"Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! "

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

![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

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

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

10/10 Excellent

"The cabin was very clean and cozy"

[](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 beautiful and spacious. Staff was super friendly. Breakfast was delicious with attentive staff keeping everything refilled and even helping my kids when I had my hands full! The property is being remodeled and that is being handled in such a way that it really was barely noticeable as a guest."

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

![Comfort Inn Glenmont - Albany South](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/314ea198_y.jpg)

### Comfort Inn Glenmont - Albany South

10/10 Excellent

"Clean and quiet"

[](https://expedia.ca/Albany-Hotels-Comfort-Inn-Glenmont-Albany-South.h11858.Hotel-Information)

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

### Berkshire Mountain Lodge

10/10 Excellent

"Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and will definitely look to return to this property in the future. "

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

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay."

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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

"Spacious 2 bed 2 bath!"

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

![Hampton Inn & Suites Albany-East Greenbush](https://images.trvl-media.com/lodging/16000000/15730000/15725300/15725242/24123a32_y.jpg)

### Hampton Inn & Suites Albany-East Greenbush

10/10 Excellent

"Staff and room were great"

[](https://expedia.ca/Albany-Hotels-Hampton-Inn-Suites-Albany-East-Greenbush.h15725242.Hotel-Information)

## Find out more about Chatham

## Chatham Vacation Homes information

| Number of reviews | 183                |
| ----------------- | ------------------ |
| Accommodation     | 490 Vacation Homes |
| Lowest Price      | CA $192            |
| Highest Price     | CA $881            |

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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)