Chatham Holiday Rentals

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Check prices for these dates

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
This weekend
10 Oct - 12 Oct
Next weekend
17 Oct - 19 Oct

Holiday Rentals in Chatham

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2048)
"Easy check in and out, clean room. "
The price is HK$764
HK$939 total
includes taxes & fees
7 Nov - 8 Nov
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)
"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."
The price is HK$1,102
HK$1,231 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
13 Oct - 14 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
22 Oct - 23 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
12 Oct - 13 Oct
Taborton Harvest Boulder Pines Cabin in the woods
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
Terrace/patio

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.

9.2 out of 10, Wonderful, (31)
"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$4,272
HK$8,151 total
includes taxes & fees
7 Nov - 8 Nov
Hancock Village Inn at Jiminy Peak
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$3,685 total
includes taxes & fees
12 Oct - 13 Oct
Comfortable Berkshires retreat on mtn resort, SISO
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
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (31)
"Great location "
The price is HK$1,300
HK$2,723 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
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
15 Oct - 16 Oct
Taborton Harvest Timber Trails Unique cabin experience
Private Yacht on Catskill Creek
Property grounds

Private Yacht on Catskill Creek

9.8 out of 10, Exceptional, (26)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is HK$1,156
HK$1,912 total
includes taxes & fees
13 Oct - 14 Oct
Private Yacht on Catskill Creek
2 bed room Apartment
Dining tables

2 bed room Apartment

10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
The price is HK$739
HK$1,387 total
includes taxes & fees
13 Oct - 14 Oct
2 bed room Apartment
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is HK$3,191
HK$5,563 total
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is HK$3,774
HK$6,240 total
includes taxes & fees
13 Oct - 14 Oct
The Lakeshore House
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Terrace/patio

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

10.0 out of 10, Exceptional, (167)
"Great property. Lots of space and activities for a large group. All amenities are well maintained and the owner was very responsive and helpful. Had a fantastic long weekend! "
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
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 Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great lodge with 1 bedroom suites and fully stocked kitchens "
Thomas 5-night trip
Posted 3 days ago
Berkshire Mountain Lodge

Find out more about Chatham

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

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

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

Frequently asked questions

Are there holiday rentals in Chatham?

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

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

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Chatham offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

How many holiday rentals are there in Chatham?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.