Old Chatham Holiday Rentals

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Check prices for these dates

Tonight
25 Nov - 26 Nov
Tomorrow
26 Nov - 27 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Holiday Rentals in Old Chatham

Exterior
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Holiday Home in Old Chatham

9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2147)
"Great place!"
United States
Nicole
The price is HK$576
HK$729 total
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is HK$1,148
HK$1,283 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,218
HK$1,361 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is HK$937
HK$1,047 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

3.0 star property
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,011
HK$1,133 total
includes taxes & fees
9 Dec - 10 Dec
Micosta Leisure Inn
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Cabin in 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$1,434 total
includes taxes & fees
26 Nov - 27 Nov
Taborton Harvest Boulder Pines Cabin in the woods
Games room
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Great Barrington

9.2 out of 10, Wonderful, (5)
The price is HK$1,576
HK$2,317 total
includes taxes & fees
1 Dec - 2 Dec
Pet Friendly Riverfront Home in Great Barrington
1 bedroom, iron/ironing board, WiFi, bed sheets
NEW Cozy Apt Bright + Modern W/D

Apartment in Hudson Park

8.8 out of 10, Excellent, (26)
"The apartment is very cozy, spacious and discreet. Perfect if your just looking for something that’s not too in the open. "
United States
D’Andre D.
The price is HK$840
HK$1,715 total
includes taxes & fees
6 Dec - 7 Dec
NEW Cozy Apt Bright + Modern W/D
Smart TV
The Rizzy Apartment

Apartment in Washington Square

7.2 out of 10, Good, (10)
"Antonio made our stay a great experience from start to finish. He was friendly, responsive, and made everything so convenient for us. The place was exactly what we needed—clean, comfortable, and in a great location.Check-in and check-out were smooth, and Antonio made sure we had everything we needed for a stress-free stay. You can really tell he cares about his guests and puts thought into making it a welcoming space.Highly recommend booking with Antonio—would definitely stay again!"
United States
Kira C.
The price is HK$1,128
HK$1,588 total
includes taxes & fees
7 Dec - 8 Dec
The Rizzy Apartment
In-room dining
cozy retreat with modern amenties

Chalet in Delmar

2.0 star property
cozy retreat with modern amenties
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

Villa in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Fridge, microwave, oven, stovetop
The Bluebirds Nest

Apartment in Washington Square

7.4 out of 10, Good, (8)
"Close to downtown and local colleges. Host was quick to answer when we had a couple of questions. "
United States
Laura C.
The price is HK$441
HK$939 total
includes taxes & fees
7 Dec - 8 Dec
The Bluebirds Nest
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Holiday Home in Lee

8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$2,977
HK$5,742 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Smart TV, books
Chic Madison Parkview

Apartment in Albany

9.6 out of 10, Exceptional, (31)
"Location close to restaurants and parks."
United States
Alex B.
The price is HK$693
HK$1,362 total
includes taxes & fees
5 Dec - 6 Dec
Chic Madison Parkview
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Interior
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Holiday Home in Catskill

9.4 out of 10, Exceptional, (18)
"The house is so historic and very beautiful/interesting. We had a great time. "
United States
Berta T.
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Holiday Home in Coxsackie

10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Holiday Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is HK$2,506
HK$5,701 total
includes taxes & fees
26 Nov - 27 Nov
Comfortable Berkshires retreat on mtn resort, SISO
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 Old Chatham Hotel Reviews

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

10/10 Excellent
"Free parking would be great "
Shahzad 1-night trip
Posted 2 days ago
Hyatt Place Albany/Downtown

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?

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!: 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 5 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.