Old Chatham Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Old Chatham

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

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
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1830)
"Love it's peace and beautiful~"
The price is ￥15,076
￥18,431 total
includes taxes & fees
Jun 22 - Jun 23
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (933)
"Amazing place!"
The price is ￥20,749
￥23,177 total
includes taxes & fees
Jun 22 - Jun 23
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

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 ￥18,841
￥20,349 total
includes taxes & fees
Jun 30 - Jul 1
Micosta Leisure Inn
The Ponds at Foxhollow
Property grounds

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 ￥33,604
￥37,536 total
includes taxes & fees
Jul 13 - Jul 14
The Ponds at Foxhollow
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (10)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is ￥15,660
￥23,821 total
includes taxes & fees
Jun 29 - Jun 30
Taborton Harvest Boulder Pines Cabin in the woods
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

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 ￥17,255
￥22,513 total
includes taxes & fees
Jun 24 - Jun 25
Deluxe Queen Room with 2 Queen Beds
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Interior

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
Mountainside Condo Ski In Ski Out
Pool

Mountainside Condo Ski In Ski Out

9.2 out of 10, Wonderful, (26)
"Perfect stay."
Mountainside Condo Ski In Ski Out
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

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!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (12)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Stay Lakeside This Summer!
Exterior

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!
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (11)
"Very kinda hosts, and wonderful house."
The price is ￥86,937
￥159,890 total
includes taxes & fees
Jul 8 - Jul 9
Hancock Village Inn at Jiminy Peak
Imagine Being Lakeside This Summer! Book Now!
Interior

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 Retreat on Robinson Pond - Stunning Sunrise
Property grounds

Lakefront Retreat on Robinson Pond - Stunning Sunrise

10.0 out of 10, Exceptional, (21)
"The house is in a great location with easy access to great food and activities. The house is extremely clean and the decor is charming and modern. Vincent was extremely communicative. All in, it was a wonderful stay and we look forward to returning!"
Lakefront Retreat on Robinson Pond - Stunning Sunrise
Exclusive Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool
cozy retreat with modern amenties
In-room dining

cozy retreat with modern amenties

2.0 star property
The price is ￥31,545
￥44,943 total
includes taxes & fees
Jun 20 - Jun 21
cozy retreat with modern amenties
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (57)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Huttopia Berkshires
Deluxe Tent | 2 bedrooms

Huttopia Berkshires

1.0 star property
Huttopia Berkshires
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 vacation rentals in Old Chatham?

Yes, we offer vacation rentals close to well known points of interest in Old Chatham, or you can choose a more remote option if you'd like a relaxing place to stay. Old Chatham is known for its museums.

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

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

How many vacation rentals will I find in Old Chatham?

With 6 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Old Chatham like?

Vacation rentals are privately owned properties you can book for several days or longer in Old Chatham. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.