Old Chatham Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Old Chatham holiday rentals

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$767
HK$1,199 total
includes taxes & fees
12 May - 13 May
Taborton Harvest Boulder Pines Cabin in the woods
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is HK$1,331
HK$2,701 total
includes taxes & fees
14 May - 15 May
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
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$768
HK$1,036 total
includes taxes & fees
14 May - 15 May
All comforts of home
Interior

Albany Retreat- Free Breakfast & Parking Included

Albany Retreat- Free Breakfast & Parking Included
West End
6.4 out of 10, (7 reviews)
"The cleanliness of the room was acceptable, but the mattress was disgusting with multiple stains on it. The furniture itself was dated and broken. I didn’t avail myself of breakfast. I did appreciate the free parking and the fact that it was very close to I-90. The picture online was clearly not the room I stayed in. It was affordable, and the property manager communication was adequate."
United States
Anonymous traveller
The price is HK$423
HK$1,049 total
includes taxes & fees
13 May - 14 May
Albany Retreat- Free Breakfast & Parking Included
Dining

The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI

The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI
Troy
9.8 out of 10, Exceptional, (13 reviews)
"Clean place, easy to navigate, coffee shop within walking distance, clear communication, very friendly! It met our needs while visiting our son. "
United States
Jamie H.
The Collar City Oasis |Pet Friendly|Workspace|Laundry|Hospitals & Colleges|WIFI
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 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$831
HK$1,107 total
includes taxes & fees
17 May - 18 May
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, (2,355 reviews)
"great stay. "
United States
John
The price is HK$675
HK$840 total
includes taxes & fees
14 May - 15 May
Vacation Village in the Berkshires
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$746
HK$833 total
includes taxes & fees
26 May - 27 May
Huttopia Berkshires
Smart TV

Cozy 1-bedroom apartment in welcoming Troy with AC

Cozy 1-bedroom apartment in welcoming Troy with AC
Troy
The price is HK$634
HK$1,095 total
includes taxes & fees
12 May - 13 May
Cozy 1-bedroom apartment in welcoming Troy with AC
Reception

cozy retreat with modern amenties

cozy retreat with modern amenties
2.0 star property
Delmar
The price is HK$1,703
HK$2,427 total
includes taxes & fees
12 May - 13 May
cozy retreat with modern amenties
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,174
HK$1,491 total
includes taxes & fees
12 May - 13 May
The Brooks Motel: Exceptional Suite
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$907
HK$1,148 total
includes taxes & fees
12 May - 13 May
Magic Forest Farm's Enchanted Cabin
Living area

Stylish Troy Apartment • Free parking • Near RPI

Stylish Troy Apartment • Free parking • Near RPI
Troy
The price is HK$1,304
HK$2,186 total
includes taxes & fees
18 May - 19 May
Stylish Troy Apartment • Free parking • Near RPI
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is HK$822
HK$1,845 total
includes taxes & fees
12 May - 13 May
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Interior

Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly

Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly
Troy
9.2 out of 10, Wonderful, (15 reviews)
"Great place! Highly recommended if you are visiting Troy "
United States
Matthew B.
The price is HK$556
HK$2,217 total
includes taxes & fees
12 May - 13 May
Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,535
HK$4,335 total
includes taxes & fees
12 May - 13 May
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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$822
HK$1,845 total
includes taxes & fees
12 May - 13 May
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$822
HK$1,845 total
includes taxes & fees
12 May - 13 May
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
1 bedroom, iron/ironing board, WiFi, bed sheets

NEW Cozy Apt Bright + Modern W/D

NEW Cozy Apt Bright + Modern W/D
Hudson Park
8.8 out of 10, Excellent, (32 reviews)
"Quiet and comfortable. Host was easy to communicate with- would definitely stay here again. "
United States
victoria c.
The price is HK$846
HK$1,674 total
includes taxes & fees
12 May - 13 May
NEW Cozy Apt Bright + Modern W/D
Smart TV

Brilliant 2-bedroom apartment with AC in vibrant Troy

Brilliant 2-bedroom apartment with AC in vibrant Troy
TROY
The price is HK$606
HK$1,194 total
includes taxes & fees
1 Jun - 2 Jun
Brilliant 2-bedroom apartment with AC in vibrant Troy
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Chatham Hotel Reviews

Berkshires Untold

Berkshires Untold

6/10 Okay
"Property is unique due to motel-style layout. Appeals to younger crowd who enjoy the lobby bar. First floor rooms could be noisy, especially near entrance to lobby. Not appropriate for people with limited mobility. "
Karen 2-night trip
Posted 8 hours ago
Berkshires Untold

Find out more about Old Chatham

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

  • View our selection of featured holiday rentals in Old Chatham
  • Use the map to find apartments and other holiday homes in the Old Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Chatham while they last

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

Frequently asked questions

Are there holiday rentals in Old Chatham?

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

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

Beautiful Estate: Week of 8/30 still open to enjoy pool, pond, trails & more!: This highly rated holiday home rental in Old Chatham is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a library so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Old Chatham?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Old Chatham stay.

What’s there to see and do in Old Chatham?

Enjoy the area's cultural attractions such as Shaker Museum and Library, or get outdoors into nature at a spot like Kinderhook Lake. Queechy Lake and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What’s a holiday rental in Old Chatham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Chatham. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.