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Top Holiday Rentals in Old Chatham

5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!

9.6 out of 10, Exceptional, (87)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1837)
"second time stayed here. Love it!"
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (937)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
The price is £131
includes taxes & fees
25 Jun - 26 Jun
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (104)
"We had an excellent stay, and would certainly book this place again!"
The price is £157
includes taxes & fees
15 Jul - 16 Jul
Micosta Leisure Inn

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The price is £189
includes taxes & fees
13 Jul - 14 Jul
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is £124
includes taxes & fees
29 Jun - 30 Jun
Taborton Harvest Boulder Pines Cabin in the woods

cozy retreat with modern amenties

2.0 star property
The price is £229
includes taxes & fees
26 Jun - 27 Jun
cozy retreat with modern amenties

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is £118
includes taxes & fees
29 Jun - 30 Jun
Deluxe Queen Room with 2 Queen Beds

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is £134
includes taxes & fees
26 Jun - 27 Jun
Taborton Harvest Timber Trails Unique cabin experience

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Mountainside Condo Ski In Ski Out

9.2 out of 10, Wonderful, (26)
"Perfect stay."
Mountainside Condo Ski In Ski Out

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (15)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (162)
"W had a birthday party for my fiancé this past weekend at Jody’s Hudson Hideaway and we had the best time! The house and property is amazing and everything is top notch. Highly recommend this place!!!"
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Delightful property, worked well for our needs"
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (118)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (144)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Chic Madison Parkview

9.8 out of 10, Exceptional, (18)
"Close to a lot of local businesses and was a cute apartment. Would stay here again. "
The price is £132
includes taxes & fees
26 Jun - 27 Jun
Chic Madison Parkview

Imagine Being Lakeside This Summer! Book Now!

10.0 out of 10, Exceptional, (16)
"Had a great trip. House was perfect for our group. Comfy beds, great fireplace and nice location near lots of local attractions."
Imagine Being Lakeside This Summer! Book Now!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (73)
"Great location near town and on a pretty lake. Owners easy to deal with and very responsive. Our family had a great trip to the Berkshires!"
Stay Lakeside This Summer!
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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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?

Deluxe Queen Room with 2 Queen Beds: This holiday home rental outside of Old Chatham is equipped with an outdoor pool, air conditioning and WiFi to help you feel comfortable during your stay.

How many holiday rentals will I find in Old Chatham?

With 6 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. The Mac-Haydn Theatre and Queechy Lake 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.