Chatham Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Chatham holiday rentals

Terrace/patio

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

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 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
scott B.
The price is HK$1,959
HK$2,492 total
includes taxes & fees
27 Apr - 28 Apr
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is HK$1,371
HK$2,431 total
includes taxes & fees
27 Apr - 28 Apr
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Outdoor dining

Private Yacht on Catskill Creek

Private Yacht on Catskill Creek
Catskill
9.8 out of 10, Exceptional, (28 reviews)
"Host was very responsive and ensured a fun stay for us."
United States
Yannie C.
The price is HK$1,164
HK$2,233 total
includes taxes & fees
3 May - 4 May
Private Yacht on Catskill Creek
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$731
HK$817 total
includes taxes & fees
26 May - 27 May
Huttopia Berkshires
View from property

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (209 reviews)
"Everything was great we can’t wait to return !"
United States
Diana
The price is HK$1,128
HK$1,557 total
includes taxes & fees
26 May - 27 May
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Room

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

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$987
HK$1,444 total
includes taxes & fees
27 Apr - 28 Apr
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Dining

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is HK$1,265
HK$2,365 total
includes taxes & fees
28 Apr - 29 Apr
Pet-Friendly Hudson Escape w/ Hot Tub
Exterior

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

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.8 out of 10, Exceptional, (38 reviews)
"The house was beautiful, clean, and filled with helpful amenities! "
United States
John C.
The price is HK$1,192
HK$2,677 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (31 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is HK$832
HK$1,108 total
includes taxes & fees
27 Apr - 28 Apr
All the comforts of home
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,336 reviews)
"great stay. "
United States
John
The price is HK$676
HK$841 total
includes taxes & fees
29 Apr - 30 Apr
Vacation Village in the Berkshires
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$769
HK$1,036 total
includes taxes & fees
27 Apr - 28 Apr
All comforts of home
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 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
Lea
The price is HK$979
HK$1,435 total
includes taxes & fees
27 Apr - 28 Apr
Taborton Harvest Boulder Pines Cabin in the woods
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (23 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
The price is HK$1,410
HK$2,756 total
includes taxes & fees
27 Apr - 28 Apr
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is HK$862
HK$1,711 total
includes taxes & fees
11 May - 12 May
Charming loft cottage in tranquil Germantown with WiFi, AC
Interior

Magic Forest Farm's Enchanted Cabin

Magic Forest Farm's Enchanted Cabin
Coeymans Hollow
9.4 out of 10, Exceptional, (9 reviews)
"Such a cute little cabin. Great place to get some rest to break up a long drive. "
United States
Anonymous traveller
The price is HK$878
HK$1,117 total
includes taxes & fees
27 Apr - 28 Apr
Magic Forest Farm's Enchanted Cabin
Terrace/patio

Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill

Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"AMAZING HOUSE FOR COUPKES AND 2 couples!!!! Amazing vibes and area. Host responds VERY quickly and is keen to help out all the time"
United States
Michael Z.
The price is HK$1,247
HK$3,192 total
includes taxes & fees
27 Apr - 28 Apr
Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,587
HK$2,446 total
includes taxes & fees
27 Apr - 28 Apr
Home in Great Barrington
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$1,026
HK$2,101 total
includes taxes & fees
30 Apr - 1 May
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,134
HK$5,461 total
includes taxes & fees
27 Apr - 28 Apr
Guesthouse Cabin vacation rentals in Berkshire County
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,587
HK$2,481 total
includes taxes & fees
29 Apr - 30 Apr
Cozy Riverside Berkshires Retreat
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

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent
"Clean room, great breakfast."
Rolf 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
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  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Spacious rustic house in Chatham, NY: This highly rated holiday home rental in Chatham offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Chatham?

With 14 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.