Old Chatham Holiday Rentals

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Tonight
5 Oct - 6 Oct
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6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Holiday Rentals in Old Chatham

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Outdoor banquet area

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (91)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2039)
"Really nice place at a reasonable price"
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, (981)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is HK$1,078
HK$1,205 total
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is HK$763
HK$852 total
includes taxes & fees
7 Oct - 8 Oct
Huttopia Berkshires
The Ponds at Foxhollow
Indoor pool, outdoor pool, pool umbrellas, pool loungers

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (124)
"Great stay!"
The price is HK$1,011
HK$1,133 total
includes taxes & fees
7 Oct - 8 Oct
Micosta Leisure Inn
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is HK$973
HK$1,425 total
includes taxes & fees
7 Oct - 8 Oct
Taborton Harvest Boulder Pines Cabin in the woods
cozy retreat with modern amenties
In-room dining

cozy retreat with modern amenties

2.0 star property
The price is HK$1,693
HK$2,412 total
includes taxes & fees
7 Oct - 8 Oct
cozy retreat with modern amenties
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

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
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is HK$3,502
HK$6,389 total
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (29)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is HK$4,661
HK$8,646 total
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak
The Bluebirds Nest
Fridge, microwave, oven, stovetop

The Bluebirds Nest

7.8 out of 10, Good, (6)
"My family stays at a lot of VRBOs and I have never had a host as accommodating and patient as Antonio. He was quick to respond and even came to the VRBO when I locked myself out."
The price is HK$441
HK$939 total
includes taxes & fees
7 Oct - 8 Oct
The Bluebirds Nest
The Rizzy Apartment
Smart TV

The Rizzy Apartment

7.2 out of 10, Good, (7)
"Great time "
The price is HK$938
HK$1,350 total
includes taxes & fees
15 Oct - 16 Oct
The Rizzy Apartment
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is HK$1,253
HK$3,693 total
includes taxes & fees
7 Oct - 8 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Rose Cottage
Outdoor dining

Rose Cottage

9.2 out of 10, Wonderful, (9)
"It's so peaceful there. It was lovely."
Rose Cottage
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

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 HK$973
HK$1,425 total
includes taxes & fees
7 Oct - 8 Oct
Taborton Harvest Timber Trails Unique cabin experience
NEW Cozy Apt Bright + Modern W/D
1 bedroom, iron/ironing board, WiFi, bed sheets

NEW Cozy Apt Bright + Modern W/D

8.6 out of 10, Excellent, (24)
"Good location and well maintained "
The price is HK$685
HK$1,513 total
includes taxes & fees
3 Nov - 4 Nov
NEW Cozy Apt Bright + Modern W/D
Mid-century Cozy Retreat W/D
Interior

Mid-century Cozy Retreat W/D

8.0 out of 10, Very good, (6)
"Walking distance to everything!! "
The price is HK$934
HK$1,773 total
includes taxes & fees
24 Oct - 25 Oct
Mid-century Cozy Retreat W/D
Chic Madison Parkview
Smart TV, books

Chic Madison Parkview

9.6 out of 10, Exceptional, (27)
"the apartment was in a great location, easy check-in, very simple check-in"
The price is HK$693
HK$1,362 total
includes taxes & fees
7 Oct - 8 Oct
Chic Madison Parkview
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"The location off the MA Pike is perfect. The woodwork and hallway carpets are dated but clean. The bedroom was clean and bed very comfortable. The surprise was the restaurant on premise, Mint. Best Indian food we have ever had! "
Linda A 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Old Chatham

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: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS: 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 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. 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.