Title: Chatham Vacation Rentals from CA $151: Short-Term Rentals for 2025 | Expedia.ca

  

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# Chatham Vacation Rentals

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## Check prices for these dates

Tonight

[Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-10-03&endDate=2025-10-05&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)

![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.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)

![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

8.6/10

Excellent

(2017)

"All around loved everything about the place! "

CA $127

CA $157 total

includes taxes & fees

Oct 7 - Oct 8

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

![Standard Cabin, 1 Queen Bed | Exterior](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/b243e122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Cabin, 2 Queen Beds | Private kitchen](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/e80152cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/02fdd0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/38acb86c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Postcard Cabins Eastern Catskills

Catskill

9.4/10

Exceptional

(83)

"My girls and I had a great time, so peaceful, clean and safe! "

CA $206

CA $275 total

includes taxes & fees

Sep 29 - Sep 30

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

![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)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/9c53d20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

Hancock

8.2/10

Very good

(979)

"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"

CA $206

CA $230 total

includes taxes & fees

Oct 19 - Oct 20

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

![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/b96863a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Huttopia Berkshires

Williamstown

10/10

Exceptional

(4)

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

CA $136

CA $151 total

includes taxes & fees

Sep 25 - Sep 26

[](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)

![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)

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

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(130)

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

[](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/40000000/39670000/39665000/39664922/5d3c366a.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)

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

### Micosta Leisure Inn

Hudson

9.2/10

Wonderful

(121)

"Great stay!"

CA $180

CA $201 total

includes taxes & fees

Sep 25 - Sep 26

[](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)

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

![Living area](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/2c4a26d5.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)

### Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

10/10

Exceptional

(12)

"Such a sweet spot in the woods! Can’t wait to come back."

CA $173

CA $253 total

includes taxes & fees

Sep 26 - Sep 27

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

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/a10f3374.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/e19375ff.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

(29)

"Great location "

CA $323

CA $585 total

includes taxes & fees

Sep 26 - Sep 27

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

![Exterior](https://images.trvl-media.com/lodging/110000000/109440000/109435000/109434975/e43d10e1.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)

![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)

### Comfortable Berkshires retreat on mtn resort, SISO

Hancock

8.8/10

Excellent

(6)

"Kind and responsive host."

CA $223

CA $656 total

includes taxes & fees

Sep 25 - Sep 26

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/d7946d7a.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)

![Lobby](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/aa306e51.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)

"Loved the property. Perfect for our gathering."

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

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512222/c3c41951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512222/w1024h671x0y6-b447aa44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512222/w905h683x60y0-e3e24bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512222/w678h683x173y0-71617839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Yacht on Catskill Creek

Catskill

8.8/10

Excellent

(10)

"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "

CA $180

CA $308 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Catskill-Hotels-Charming-Yacht-On-Catskill-Creek.h93512222.Hotel-Information)

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

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/378fd21d.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)

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

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

Lee

CA $449

CA $926 total

includes taxes & fees

Oct 1 - Oct 2

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

![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)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.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)

### Hancock Village Inn at Jiminy Peak

Hancock

10/10

Exceptional

(13)

"Amazing Inn. Cozy and everything we needed. "

CA $829

CA $1,537 total

includes taxes & fees

Sep 25 - Sep 26

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

![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.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)

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

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

Lenox

9.0/10

Wonderful

(28)

"Beautiful, spacious house in a great location!"

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

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90210000/90207600/90207573/w1024h676x0y3-56d55a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/90210000/90207600/90207573/w1024h675x0y4-379e6630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90210000/90207600/90207573/w1024h675x0y3-cb40d10d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90210000/90207600/90207573/w906h683x59y0-2659829d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rose Cottage

Leeds

9.0/10

Wonderful

(8)

"It's so peaceful there. It was lovely."

[](https://www.expedia.ca/Leeds-Hotels-Rose-Cottage.h90207573.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)

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

![Exterior](https://images.trvl-media.com/lodging/34000000/33550000/33547100/33547021/080f9414.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)

### BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Old Chatham

9.6/10

Exceptional

(91)

"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "

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

![TV](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/8848cb67.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)

![Exterior](https://images.trvl-media.com/lodging/104000000/103280000/103270900/103270843/w907h683x59y0-ef358a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lakeshore House

Niverville

10/10

Exceptional

(1)

"Excellent stay!"

CA $670

CA $1,109 total

includes taxes & fees

Sep 26 - Sep 27

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/2c6abeb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/ba127977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/d7345ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102613300/102613211/cfbd9c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Taborton Harvest Timber Trails Unique cabin experience

Sand Lake

10/10

Exceptional

(1)

"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."

CA $173

CA $253 total

includes taxes & fees

Sep 26 - Sep 27

[](https://www.expedia.ca/Sand-Lake-Hotels-Taborton-Harvest-Timber-TrailsUnique-Cabin-Experience.h102613211.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/13f82703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/edf60411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

10/10

Exceptional

(9)

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

CA $510

CA $953 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.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)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/417057d6.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)

![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)

### Private Yacht on Catskill Creek

Catskill

9.8/10

Exceptional

(26)

"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."

CA $205

CA $340 total

includes taxes & fees

Sep 28 - Sep 29

[](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

![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

"The lobby was different and dramatic. Liked that the eating area was raised above it on the second floor and gave a view of the hotel and surrounding scenery. Breakfast was adequate - nothing special but good. We did have a bit of trouble with the toilet in our room which we were able to fix without calling the desk. Would definitely stay there again if we return to visit."

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

![Four Points by Sheraton Albany](//images.trvl-media.com/lodging/55000000/54080000/54077800/54077744/55bb8198_y.jpg)

### Four Points by Sheraton Albany

10/10 Excellent

"Just a lovely place by the airport like 15 minutes. Comfy bed and very quiet. All the staff were exceptionally nice. In the bar I had Andrew as my bartender. He made me the most wonderful drink and wrote down for me how he made it!! He was very entertaining and nice! I will definitely stay there again. Ps- the guy at front desk- I didn’t catch his name. He too was so helpful to us so thank you!"

[](https://expedia.ca/Albany-Hotels-Four-Points-By-Sheraton-Albany.h54077744.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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

"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."

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

![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg)

### Jiminy Peak Mountain Resort

10/10 Excellent

"Absolutely beautiful "

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Excellent location. Friendly staff. "

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

![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Perfect for an overnight for the Tanglewood concert"

[](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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

"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. "

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

![Postcard Cabins Eastern Catskills](//images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/fe54355c_y.jpg)

### Postcard Cabins Eastern Catskills

10/10 Excellent

"The things I’ve loved about the experience were the cleanliness of the cabin, along with easy parking. There was nothing that I didn’t like about the experience, definitely would have to go there again."

[](https://expedia.ca/Catskill-Hotels-Postcard-Cabins-Eastern-Catskills.h109129528.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 $151 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)
-   [Cabin Rentals in Chatham](https://expedia.ca/Chatham-Cabins.d6046736-aaCabins.Travel-Guide-Accommodation)
-   [B&B in Chatham](https://expedia.ca/Chatham-Bed-And-Breakfast.d6046736-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Resorts in Chatham](https://expedia.ca/Chatham-Resort-Hotels.d6046736-aaResortHotels.Travel-Guide-Accommodation)
-   [Farmstay in Chatham](https://expedia.ca/Chatham-Agritourism.d6046736-aaAgritourism.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?

> [Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information): This vacation home rental near Chatham is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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

> With 12 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,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFRUlEQVR4Xu3bQZLbNhBGYbiy0DJH4FF0NPBoOgqP4OUspgZR/2igIUoep1PlLGbe21jTauLjjkM7Ke1/qJwHfyKQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpFqQ93JqG6Mfrd3K5b58H6mfNr22t3K//LDPtY/WapwMUkDOayC9GieDFJDzGkivxslfFanxk04M99qHR798RfzCn3Yrs8ezQEBAQCwQBaJAZr6rLhOp/cubTX1xL/7Y1+iwPxzR6PFCCwQExP4AASkgIN7niPLLL3Nrpi0FAlJAQDyQ2FIgIOU/IHsf6H16uq19zFEpf9kAZLPp3gcgCgQEBATk1ge/Q6K565dflu+81dXWDASkgXggEYgCAWln5LEn5PPRqRong7wYnapxMsiL0akaJ4O8GJ2qcTLIi9GpGieDvBidqnEyyIvRqRonL8iLdLnSia0d4326+Cv2HH0WCMiLQE6BgLwI5NTXRXR5sRNL2Qzx/ER3HWl9qy1/D66Rqv1ATeKjAhlbGqnaD9QkPiqQsaWRqv1ATeKjAhlbGqnaD9QkPiqQsaWRqv1ATeKjAhlbGqnaD9QkPiqQsaWRqv1ATeJjs92/+z8dq6Nvr6OJ/LDPcn1L/8X1OqrjChAQBQLSQEBARgvyPrbLfMY3c3X5zUbzciE+8gvjVuynx7duEBAQEJCr/Wg/gYDYJD76rnrrj2rf1eVv9vU2tw0pc2tfLgQB8UAaCAgIyL9B7OmtLk3P+CdXrSf6yPrwC5e780BOIwsEBATEAjmNrG+GeB/+QLddpRNv3S398riVeaLeuuX63VU/r4GAzEBAQEBA1COy9xOV7zril0/kx3S3/rXceXfamoGANBAFAgLSQNSCvNtz2S8vfTe6armfuBf9m7O7fiu+td7KDAQEBMT2QBSILYPER0eeduWuJ/qtnPvo1ywnjkBAQEYgIKdAQJo9veMV+zx6RMattHbY57OrrRkISAMBeTECaSAg+qIU/5+U/MToZgM7MR77PprpGX+5H1n8l4MZCAjICCQCUSAgQiI7UekZf+uft76qZ7yaW/pL79v4DKK2vgoCAtIDUSBq66sgMz2qo9pH1/7lsYz0QPf2ol8O1BzOnkcgIFbto2v/8lhGIBYIiFX76Nq/PJYRiPUFkPflxLe5u/cr50hbesY/buk3gZmf5YGAgPQtEAUCAvKE6O+um11eyvYwsuVRnDi3/O5865ev2CAgINexBWLLIPER5Nsjt3KZ072fuI5aW5/xxzhRyHp3MxAQEBAQEJDPEN+1b8auTlR2otJfZ2vLL1zzLTvLAwEBAdE3ICCPl4P8okD86e0JKeVit6Jq35+/CfgNeyAgLwIBAbFAQN6XU9Q2vvl4ROoYNUO2cSt6N/f8rdsDAQEB6W3jG5ARCIh2o4k8Xb4X/a9M3mHT2j/PrRhZICAgy4lzK0YWCAjIcuLcipH1dRG9T/vL82Yje5+ODkOseOz7lnfpWwXEApmBgICAgKQRnWjL9wJR7u79Vm59qAvrOBcEBASkgIAUkCSirlq+j5S2/Bkvdy/rW/c5EI1AQAoIyFMgGoFEfqJdvp4YXZflfRnNW5mBaBTtywgExAPRKNqXEQiI91WRxzab2stzvGLPUbP36Yv9cdiq/XKgZ/zbfOteAmkgJwMEBMQDad8e+XOBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJNXXQf4Bg0EK8Qv8B7MAAAAASUVORK5CYII=)