Search Holiday Rentals in Chatham

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Check prices for these dates

Tonight
3 Jul - 4 Jul
Tomorrow
4 Jul - 5 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Holiday Rentals in Chatham

We don't have any properties that match your exact search

Recommended hotels in Chatham

The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (84)
"Beautiful room and property. Perfect weekend getaway!"
The price is ฿9,384
฿11,323 total
includes taxes & fees
6 Jul - 7 Jul
The Old Inn On The Green
Pilgrim Inn
1 bedroom, individually decorated, individually furnished, desk

Pilgrim Inn

2.5 star property
5.8 out of 10, (308)
"Great location but no staff at check-in or checkout!"
The price is ฿2,880
฿3,217 total
includes taxes & fees
31 Jul - 1 Aug
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff, easy parking"
The price is ฿3,823
฿4,270 total
includes taxes & fees
21 Jul - 22 Jul
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (385)
"No frills but it was a great stay!"
The price is ฿3,074
฿3,434 total
includes taxes & fees
9 Jul - 10 Jul
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (733)
"Shampoo and toilet paper should have been In the room."
The price is ฿2,301
฿2,570 total
includes taxes & fees
17 Jul - 18 Jul
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (367)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (604)
"Good location. Nice for an evening after a show at Tanglewood. "
The price is ฿2,063
฿2,304 total
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great place"
The price is ฿6,298
฿7,035 total
includes taxes & fees
13 Jul - 14 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (664)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is ฿5,109
฿6,158 total
includes taxes & fees
9 Jul - 10 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 ฿8,955
฿10,003 total
includes taxes & fees
5 Jul - 6 Jul
The Ponds at Foxhollow
Holiday Inn Express & Suites Pittsfield - Berkshires
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is ฿4,923
฿5,499 total
includes taxes & fees
8 Jul - 9 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is ฿7,269
฿8,120 total
includes taxes & fees
6 Jul - 7 Jul
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (606)
"Fix sink faucet in room #2. Otherwise worked great for just a place to sleep. Shower made up for having to shave in cold water."
The price is ฿2,233
฿2,494 total
includes taxes & fees
6 Jul - 7 Jul
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (747)
"Was great loved the jacuzzi tub "
The price is ฿3,203
฿3,578 total
includes taxes & fees
6 Jul - 7 Jul
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (501)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Everyone was very nice to us! "
The price is ฿6,593
฿7,364 total
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (742)
"Great boutique hotel"
The price is ฿6,115
฿6,831 total
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Nice place to stay. Good breakfast. "
The price is ฿5,198
฿5,806 total
includes taxes & fees
13 Jul - 14 Jul
The Yankee, Trademark Collection by Wyndham
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (292)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is ฿3,850
฿4,301 total
includes taxes & fees
28 Jul - 29 Jul
The Central Downtown Inn & Suites
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 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.

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.