Title: Chatham Vacation Rentals from $141: Search Short-Term Rentals | Expedia.com

[Chatham Travel Guide](https://expedia.com/Chatham.dx6046736)[Hotels in Chatham](https://expedia.com/Chatham-Hotels.d6046736.Travel-Guide-Hotels)[Flights to Chatham](https://expedia.com/Cheap-Flights-To-Chatham.d6046736.Travel-Guide-Flights)[Car Rentals in Chatham](https://expedia.com/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.com/Chatham.d6046736.Destination-Travel-Guides)

![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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We are not like the others - we include taxes and fees

## Check prices for these dates

In two weeks

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

In two months

[Jun 5 - Jun 7](https://www.expedia.com/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)

In three months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6046736&startDate=2026-07-31&endDate=2026-08-02&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 rentals

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/143defff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/21a1823e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/2da92659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/dd92adc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BLUSH: Boutique TINY home\*private spa\*walk to town

[](https://www.expedia.com/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

Chatham

10/10

Exceptional

(7 reviews)

"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"

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

scott B.

$293 nightly

$330 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/aba54efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/504a6d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/ece507a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/324c211f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Shack - 300 square feet of pure sweetness.

[](https://www.expedia.com/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

Chatham

10/10

Exceptional

(3 reviews)

"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "

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

Sue G.

$327 nightly

$369 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/dc6494b1.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)

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

![Living area](https://images.trvl-media.com/lodging/125000000/124470000/124466500/124466418/34a7dcb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Chatham

9.0/10

Wonderful

(2 reviews)

"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "

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

Rochelle F.

$276 nightly

$309 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/94000000/93500000/93498000/93497976/w1016h683x4y0-1acbabd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93500000/93498000/93497976/w378h683x323y0-1b2b11d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/94000000/93500000/93498000/93497976/w905h683x59y0-4ba2fabc.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/94000000/93500000/93498000/93497976/w1019h683x5y0-14de5d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Yacht on Catskill Creek

[](https://www.expedia.com/Catskill-Hotels-Beautiful-Yacht-On-Catskill-Creek.h93497976.Hotel-Information)

Catskill

10/10

Exceptional

(21 reviews)

"So much fun for me and my boys to stay. AJ and Melissa are great hosts!"

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

Amy G.

$253 nightly

$283 total

May 1 - May 2

Total with taxes and fees

[](https://www.expedia.com/Catskill-Hotels-Beautiful-Yacht-On-Catskill-Creek.h93497976.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/w905h683x59y0-95e40043.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)

![Beach towels](https://images.trvl-media.com/lodging/94000000/93520000/93512300/93512221/c74b0c89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Yacht on Catskill Creek

[](https://www.expedia.com/Catskill-Hotels-Private-Yacht-On-Catskill-Creek.h93512221.Hotel-Information)

Catskill

9.8/10

Exceptional

(28 reviews)

"Host was very responsive and ensured a fun stay for us."

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

Yannie C.

$242 nightly

$271 total

May 1 - May 2

Total with taxes and fees

[](https://www.expedia.com/Catskill-Hotels-Private-Yacht-On-Catskill-Creek.h93512221.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/d4631129.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/d71945c1.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/110000000/109130000/109129600/109129528/87fd867b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/110000000/109130000/109129600/109129528/eb59c690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Catskill

9.6/10

Exceptional

(191 reviews)

"We had the best time! "

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

Eric

$179 nightly

$193 total

Apr 13 - Apr 14

Total with taxes and fees

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

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

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

Williamstown

8.8/10

Excellent

(2,324 reviews)

"Clean rooms, and very friendly staff"

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

Amr

$126 nightly

$141 total

Apr 12 - Apr 13

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/5d3c366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/818a652c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8. The Riverview Room | Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/40000000/39670000/39665000/39664922/40f18d40.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

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

Hudson

9.2/10

Wonderful

(142 reviews)

"Steven is the most helpful and kind host I've ever experienced! The property is lovely, and the rooms are cozy. I would definitely recommend staying here especially as a solo traveler."

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

Salvio

$133 nightly

$150 total

Apr 7 - Apr 8

Total with taxes and fees

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

![Room](https://images.trvl-media.com/lodging/128000000/127360000/127356900/127356865/3b0f280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/128000000/127360000/127356900/127356865/152c85eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/128000000/127360000/127356900/127356865/c76c9e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/128000000/127360000/127356900/127356865/3f37c158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

[](https://www.expedia.com/Sand-Lake-Hotels-Taborton-Harvest-Fiddlehead-Cabin-In-Cool-Sand-Lake-Perfect-For-Relaxing-Getaway.h127356865.Hotel-Information)

Sand Lake

$166 nightly

$184 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Sand-Lake-Hotels-Taborton-Harvest-Fiddlehead-Cabin-In-Cool-Sand-Lake-Perfect-For-Relaxing-Getaway.h127356865.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c1a3192b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.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.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

Stephentown

$499 nightly

$554 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/41313771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/90-e74888f2.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/60000000/59990000/59987600/59987529/97b8d9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/59990000/59987600/59987529/90-d8c61953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All comforts of home

[](https://www.expedia.com/Hudson-Hotels-All-Comforts-Of-Home.h59987529.Hotel-Information)

Hudson

9.6/10

Exceptional

(55 reviews)

"Loved the place and would love to come back. "

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

Georgine

$118 nightly

$132 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Hudson-Hotels-All-Comforts-Of-Home.h59987529.Hotel-Information)

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

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/3e6e58ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

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

Sheffield

10/10

Exceptional

(42 reviews)

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

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

Kelly R.

$451 nightly

$504 total

Apr 7 - Apr 8

Total with taxes and fees

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

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Guesthouse Cabin vacation rentals in Berkshire County

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

Sheffield

10/10

Exceptional

(10 reviews)

"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "

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

deborah d.

$614 nightly

$686 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Stockbridge

10/10

Exceptional

(35 reviews)

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

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

Susan

$650 nightly

$726 total

Apr 8 - Apr 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/3898d01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/9a68bfc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/ea8d2754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113400000/113393600/113393517/fc504833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming loft cottage in tranquil Germantown with WiFi, AC

[](https://www.expedia.com/Germantown-Hotels-Charming-Loft-Cottage-In-Tranquil-Germantown-With-WiFi.h113393517.Hotel-Information)

Germantown

10/10

Exceptional

(10 reviews)

"Very clean, comfortable, good location, great communication with host. "

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

Lisa B.

$189 nightly

$212 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Germantown-Hotels-Charming-Loft-Cottage-In-Tranquil-Germantown-With-WiFi.h113393517.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/30153bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/2c4a26d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101310000/101301800/101301745/8d5d0ff1.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)

### Taborton Harvest Boulder Pines Cabin in the woods

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

Sand Lake

10/10

Exceptional

(15 reviews)

"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "

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

Lea

$165 nightly

$183 total

Apr 7 - Apr 8

Total with taxes and fees

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

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

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

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/69c2e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

Great Barrington

10/10

Exceptional

(4 reviews)

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

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

Roberta

$1,193 nightly

$1,332 total

Apr 7 - Apr 8

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/8b34823f.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/b9c0be0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117390000/117382300/117382215/9510eac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Lee

8.8/10

Excellent

(3 reviews)

"House was clean and made our Thanksgiving great with it's size and amenities. "

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

Khalil S.

$711 nightly

$794 total

Apr 13 - Apr 14

Total with taxes and fees

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

![TV, fireplace](https://images.trvl-media.com/lodging/39000000/38110000/38105100/38105057/fe02096d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38110000/38105100/38105057/125c9b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/39000000/38110000/38105100/38105057/0a2f485f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/39000000/38110000/38105100/38105057/d9ba6eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A stunning, modern Lodge with rustic charm at June Farms!

[](https://www.expedia.com/West-Sand-Lake-Hotels-A-Stunning.h38105057.Hotel-Information)

West Sand Lake

10/10

Exceptional

(5 reviews)

"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"

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

LisaL

$703 nightly

$780 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/West-Sand-Lake-Hotels-A-Stunning.h38105057.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/9ea3f9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/223b5082.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)

![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)

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

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

Catskill

9.8/10

Exceptional

(38 reviews)

"The house was beautiful, clean, and filled with helpful amenities! "

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

John C.

$303 nightly

$339 total

Apr 12 - Apr 13

Total with taxes and fees

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

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-20&endDate=2026-04-21&regionId=6046736&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VILLA)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=HOUSE_BOAT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Chatham%2C+New+York%2C+United+States+of+America&regionId=6046736&latLong=42.36425%2C-73.594841&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CHALET)

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## Top Chatham Hotel Reviews

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

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

8/10 Good

"Breakfast was great room was clean. Key didn’t work when I got there they asked me to come back down. Bringing new key up would have been a bit better so I didn’t have to. That was a big expectation for price paid. "

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

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

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

10/10 Excellent

"It was an overall good experience. Hot water was limited make sure to take a shower early in the morning. WiFi was good"

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

![Comfort Inn Glenmont - Albany South](https://images.trvl-media.com/lodging/1000000/20000/11900/11858/8d1e9400_y.jpg)

### Comfort Inn Glenmont - Albany South

8/10 Good

"The hotel was undergoing construction. The shower was excellent, great water pressure and heat. My husband and I both thought it was a great shower, one of the better ones we have experienced traveling. The breakfast was also excellent. "

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

![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg)

### Quality Inn Great Barrington

8/10 Good

"Room and bed were clean as I would expect bath and toilet were clean, shower pressure was mediocre as I usually expect. Location was excellent as my ski resorts were within close proximity as well as restaurants (think Bogies, awesome food and reasonable prices). Check in was a breeze and Brian the manager was quite pleasant and informative. Will stay again on my next ski trip in the area."

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

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Love that place. Does need a little sprucing up. Staff great and accomodating "

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

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

### Berkshires Untold

10/10 Excellent

"Very clean and updated. Park right outside your room. Nice bar with outdoor fireplace. Staff was amazing. Simple put, great place to stay!"

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

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

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

6/10 Okay

"Great dinner, nice room. Only complaint is that none of the 3 elevators would come to the 6 floor in the morning. It was a long walk with our baggage."

[](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

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

### Vacation Village in the Berkshires

8/10 Good

"Beds could be more updated"

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

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

### Hotel On North

10/10 Excellent

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

[](https://expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.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, apartments, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.com/Chatham-Private-Vacation-Homes.d6046736-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chatham ](https://expedia.com/Chatham-Cottages.d6046736-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chatham ](https://expedia.com/Chatham-Apartments.d6046736-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Chatham ](https://expedia.com/Chatham-Condos.d6046736-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Chatham ](https://expedia.com/Chatham-Cabins.d6046736-aaCabins.Travel-Guide-Accommodation)
- [B&B in Chatham ](https://expedia.com/Chatham-Bed-And-Breakfast.d6046736-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Motels in Chatham ](https://expedia.com/Chatham-Motels.d6046736-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Chatham ](https://expedia.com/Chatham-Guest-Houses.d6046736-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Chatham ](https://expedia.com/Chatham-Lodges.d6046736-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Chatham ](https://expedia.com/Chatham-Apart-Hotels.d6046736-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Chatham ](https://expedia.com/Chatham-Inns.d6046736-aaInns.Travel-Guide-Accommodation)
- [Chalets in Chatham ](https://expedia.com/Chatham-Chalets.d6046736-aaChalets.Travel-Guide-Accommodation)
- [Villas in Chatham ](https://expedia.com/Chatham-Villas.d6046736-aaVillas.Travel-Guide-Accommodation)
- [Houseboats in Chatham ](https://expedia.com/Chatham-Houseboats.d6046736-aaHouseboats.Travel-Guide-Accommodation)
- [RV Parks in Chatham ](https://expedia.com/Chatham-RV-Parks.d6046736-aaRVParks.Travel-Guide-Accommodation)
- [Condo Resorts in Chatham ](https://expedia.com/Chatham-Condominium-Resort.d6046736-aaCondominiumResort.Travel-Guide-Accommodation)
- [Country Houses in Chatham ](https://expedia.com/Chatham-Country-House.d6046736-aaCountryHouse.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chatham?

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

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

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

### What are vacation rentals like in Chatham?

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