Chatham Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chatham holiday rentals

Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is HK$1,751
HK$3,211 total
includes taxes & fees
13 Jan - 14 Jan 2026
HunnyHAUS: Deluxe TINY*private spa*walk to town
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

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, (6)
"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$1,556
HK$2,659 total
includes taxes & fees
6 Jan - 7 Jan 2026
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"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
Sue G.
The price is HK$1,671
HK$2,805 total
includes taxes & fees
12 Jan - 13 Jan 2026
Sugar Shack - 300 square feet of pure sweetness.
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,574
HK$1,758 total
includes taxes & fees
7 Jan - 8 Jan 2026
Huttopia Berkshires
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2195)
"I great place to stay!!"
United Kingdom
Maricel
The price is HK$808
HK$988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
Exterior
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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, (117)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is HK$852
HK$1,256 total
includes taxes & fees
15 Jan - 16 Jan 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is HK$1,010
HK$1,131 total
includes taxes & fees
1 Jan - 2 Jan 2026
Micosta Leisure Inn
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,651
HK$1,845 total
includes taxes & fees
8 Jan - 9 Jan 2026
Jiminy Peak Mountain Resort
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

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, (8)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is HK$848
HK$1,682 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds
All comforts of home

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$763
HK$1,028 total
includes taxes & fees
6 Jan - 7 Jan 2026
All comforts of home
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is HK$1,224
HK$2,886 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Outdoor spa tub
Tiny Home w/ Hot Tub and Sunset View!

Tiny Home w/ Hot Tub and Sunset View!

Tiny Home w/ Hot Tub and Sunset View!
Selkirk
10.0 out of 10, Exceptional, (2)
"Very nice place. Was in a quiet area and hosts were great."
United States
Brian H.
The price is HK$700
HK$1,008 total
includes taxes & fees
7 Jan - 8 Jan 2026
Tiny Home w/ Hot Tub and Sunset View!
Property grounds
All the comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$826
HK$1,099 total
includes taxes & fees
6 Jan - 7 Jan 2026
All the comforts of home
Dining tables
2 bed room Apartment

2 bed room Apartment

2 bed room Apartment
South End
8.8 out of 10, Excellent, (8)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is HK$739
HK$1,387 total
includes taxes & fees
5 Jan - 6 Jan 2026
2 bed room Apartment
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$957
HK$1,846 total
includes taxes & fees
5 Jan - 6 Jan 2026
Berkshires Apartment at the Stephentown Hotel
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is HK$973
HK$1,425 total
includes taxes & fees
1 Jan - 2 Jan 2026
Taborton Harvest Boulder Pines Cabin in the woods
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is HK$1,066
HK$2,347 total
includes taxes & fees
6 Jan - 7 Jan 2026
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

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, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
The price is HK$1,229
HK$2,355 total
includes taxes & fees
4 Jan - 5 Jan 2026
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,236
HK$1,567 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Brooks Motel: Exceptional Suite
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

Vacation Village in the Berkshires

10/10 Excellent
"Great place to stay!! Very clean and very professional team"
Maricel 3-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chatham offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Chatham?

With 13 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 Kinderhook Lake. 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.