Title: Chatham Vacation Rentals from CA $157: Short-Term Rentals for 2025 | Expedia.ca

 

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# Chatham Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Chatham

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2133)

"We came here because it was off season, great price, and it had an indoor pool. "

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

Monica

CA $127

CA $157 total

includes taxes & fees

Nov 25 - Nov 26

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

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

Hancock

8.2/10

Very good

(984)

"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."

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

Philip

CA $209

CA $233 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/fd380371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Private kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2d5c8478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/4ac9d6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires

Williamstown

10/10

Exceptional

(7)

"Perfect place for a relaxing getaway! We loved everything! "

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

Cammie

CA $310

CA $347 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(132)

"Perfect location "

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

krystle

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/d78d1e6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/4eca1141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/287e98ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8. The Riverview Room](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/40f18d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Micosta Leisure Inn

Hudson

9.2/10

Wonderful

(130)

"Clean, pet friendly , just an overall super nice place to stay "

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

Gail

CA $165

CA $185 total

includes taxes & fees

Nov 21 - Nov 22

[](https://www.expedia.ca/Hudson-Hotels-Micosta-Leisure-Inn.h39664922.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/a78d5e6a_edited_6c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/d249528d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/02d3bd96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/78f91337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

10/10

Exceptional

(13)

"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "

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

Barb W.

CA $175

CA $257 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Sand-Lake-Hotels-Cabin-In-The-Woods.h101301745.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa330ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/92ba9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Kemble- Built by a US Secretary of State in Lenox

Lenox

10/10

Exceptional

(17)

"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...

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

Carrie S.

[](https://www.expedia.ca/Lenox-Hotels-The-Kemble-Built-By-A-US-Secretary-Of-State-In-Lenox.h76003386.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Pet Friendly Riverfront Home in Great Barrington

Great Barrington

9.0/10

Wonderful

(4)

"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 $268

CA $397 total

includes taxes & fees

Nov 19 - Nov 20

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

![Exterior](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/c63bdc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/33ca2782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/a10f3374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/19462ffb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill

9.8/10

Exceptional

(33)

"Great location "

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

steve p.

CA $211

CA $462 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Catskill-Hotels-Cozy-Catskill-Cabin-W-10-Minute-Walk-To-Downtown-Catskill.h78321995.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c8837e7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hancock Village Inn Near Jiminy Peak

Hancock

10/10

Exceptional

(15)

"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...

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

Jim O.

CA $840

CA $1,558 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/e67896be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/3f3d1749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/fe676105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112620000/112619100/112619076/072199c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3-bedroom Cabin for nature lovers

Stephentown

7.0/10

Good

(2)

"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...

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

John O.

CA $185

CA $411 total

includes taxes & fees

Nov 19 - Nov 20

[](https://www.expedia.ca/Stephentown-Hotels-Charming-3-Bedroom-Cabin-For-Nature-Lovers.h112619076.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/58b0972d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/d06b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/636f9a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/fb68a83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5-bedroom house in charming Lee with WiFi

Lee

8.0/10

Very good

(1)

"House was large, clean, and comfortable. "

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

John Z.

CA $536

CA $1,043 total

includes taxes & fees

Nov 18 - Nov 19

[](https://www.expedia.ca/Lee-Hotels-Spacious-5-Bedroom-House-In-Charming-Lee-With-WiFi.h117382215.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/e175fcb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/a366bf74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amore Estate - beautiful room with many places to explore and relax in.

Lenox

9.2/10

Wonderful

(32)

"Beautiful property with tons of space and fantastic for a group of friends or family"

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

Greg S.

[](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information)

![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33550000/33547100/33547021/d18a944f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33550000/33547100/33547021/1221456e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33550000/33547100/33547021/5cffc772.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33547100/33547021/bd7a6d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham

9.6/10

Exceptional

(93)

"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"

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

Daisy H.

[](https://www.expedia.ca/Old-Chatham-Hotels-Beautiful-Special-5-Star-EstateReduced-Rates-For-Smaller-Groups-Inquire-Now.h33547021.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/63595554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/62b3ce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/35eff0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge

10/10

Exceptional

(132)

"Clean house, well appointed, great location, responsive owner"

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

sara m.

[](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/18066543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/f076ba69_edited_5004.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)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/6658a41d_edited_267e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable Berkshires retreat on mtn resort, SISO

Hancock

9.0/10

Wonderful

(7)

"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"

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

Henry C.

CA $226

CA $758 total

includes taxes & fees

Nov 13 - Nov 14

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

![Property grounds](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/b2718775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/fa193720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/aaeed4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/8848cb67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lakeshore House

Niverville

10/10

Exceptional

(1)

"Excellent stay!"

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

KEITARO A.

CA $680

CA $1,125 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Niverville-Hotels-The-Lodge-On-The-Lake.h103270843.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/052d8e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/70f669a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/be2467fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101470000/101469400/101469345/ed51271f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Blue Elm - A Historic Berkshire Cottage

Sheffield

10/10

Exceptional

(14)

"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...

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

Marc R.

[](https://www.expedia.ca/Sheffield-Hotels-The-Blue-Elm-A-Historic-Berkshire-Cottage.h101469345.Hotel-Information)

![Dining tables](https://images.trvl-media.com/lodging/104000000/103890000/103881900/103881881/w906h683x59y0-965c09aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103890000/103881900/103881881/72295042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/104000000/103890000/103881900/103881881/w905h683x60y0-ea8619c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi](https://images.trvl-media.com/lodging/104000000/103890000/103881900/103881881/w905h683x60y0-42259ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 bed room Apartment

South End

10/10

Exceptional

(4)

"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."

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

Sarah K.

CA $133

CA $250 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Albany-Hotels-2-Bed-Room-Apartment.h103881881.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/w905h683x59y0-e28c5983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/w906h683x58y0-0da96433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/196e00e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/w904h683x60y0-15900dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Yacht on Catskill Creek

Catskill

9.8/10

Exceptional

(28)

"It was great!"

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

Chaya S.

[](https://www.expedia.ca/Catskill-Hotels-Private-Yacht-On-Catskill-Creek.h93512221.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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## Top Chatham Hotel Reviews

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

### Vacation Village in the Berkshires

10/10 Excellent

"Good "

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

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

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

10/10 Excellent

"Early check in."

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

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

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Everything was great"

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

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Staff…great Room…great We enjoy it here and stay annually "

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

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

### Comfort Inn Glenmont - Albany South

10/10 Excellent

"All good!"

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

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg)

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

10/10 Excellent

"The room was great, with a balcony and indoor fireplace. The lake was beautiful, renting a kayak and exploring made for a great morning. The surrounding areas made things even more enjoyable, providing great hiking and scenery "

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

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

### Quality Inn

10/10 Excellent

"The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. "

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

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

10/10 Excellent

"Place was great!"

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

![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"I love the ambience - historic and comfortable and excellent food. "

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

## Find out more about Chatham

**Everything you need to know about** **Chatham** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chatham vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham vacation rentals we have selected for you start as low as CA $157 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chatham rentals**

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Vacation Homes in Chatham](https://expedia.ca/Chatham-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cottages in Chatham](https://expedia.ca/Chatham-Cottages.d6046736-aaCottages.Travel-Guide-Accommodation)
-   [Apartments in Chatham](https://expedia.ca/Chatham-Apartments.d6046736-aaApartments.Travel-Guide-Accommodation)
-   [Condo Rentals in Chatham](https://expedia.ca/Chatham-Condos.d6046736-aaCondos.Travel-Guide-Accommodation)
-   [B&B in Chatham](https://expedia.ca/Chatham-Bed-And-Breakfast.d6046736-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cabin Rentals in Chatham](https://expedia.ca/Chatham-Cabins.d6046736-aaCabins.Travel-Guide-Accommodation)
-   [Farmstay in Chatham](https://expedia.ca/Chatham-Agritourism.d6046736-aaAgritourism.Travel-Guide-Accommodation)
-   [Resorts in Chatham](https://expedia.ca/Chatham-Resort-Hotels.d6046736-aaResortHotels.Travel-Guide-Accommodation)
-   [Motels in Chatham](https://expedia.ca/Chatham-Motels.d6046736-aaMotels.Travel-Guide-Accommodation)
-   [Guest Houses in Chatham](https://expedia.ca/Chatham-Guest-Houses.d6046736-aaGuestHouses.Travel-Guide-Accommodation)
-   [Aparthotels in Chatham](https://expedia.ca/Chatham-Apart-Hotels.d6046736-aaApartHotels.Travel-Guide-Accommodation)
-   [Inns in Chatham](https://expedia.ca/Chatham-Inns.d6046736-aaInns.Travel-Guide-Accommodation)
-   [Lodges in Chatham](https://expedia.ca/Chatham-Lodges.d6046736-aaLodges.Travel-Guide-Accommodation)
-   [Chalets in Chatham](https://expedia.ca/Chatham-Chalets.d6046736-aaChalets.Travel-Guide-Accommodation)
-   [Villas in Chatham](https://expedia.ca/Chatham-Villas.d6046736-aaVillas.Travel-Guide-Accommodation)
-   [RV Parks in Chatham](https://expedia.ca/Chatham-RV-Parks.d6046736-aaRVParks.Travel-Guide-Accommodation)
-   [Houseboats in Chatham](https://expedia.ca/Chatham-Houseboats.d6046736-aaHouseboats.Travel-Guide-Accommodation)
-   [Condo Resorts in Chatham](https://expedia.ca/Chatham-Condominium-Resort.d6046736-aaCondominiumResort.Travel-Guide-Accommodation)
-   [Country Houses in Chatham](https://expedia.ca/Chatham-Country-House.d6046736-aaCountryHouse.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chatham?

> Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

### What are some of the best vacation home rentals that Chatham has to offer?

> [Pet Friendly Riverfront Home in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information): This vacation home near Chatham is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

### How many vacation rentals are there in Chatham?

> With 13 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

### What can I see and do in Chatham?

> While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

### What are vacation rentals like in Chatham?

> Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)