Photo by Shirley Rhodes

Brattleboro Holiday Rentals

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Holiday Rentals in Brattleboro

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is S$549
includes taxes & fees
24 Nov - 25 Nov
Long Trail House at Stratton Mountain Resort
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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Other types of properties in Brattleboro you may be interested in

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"The staff are nice "
The price is S$156
includes taxes & fees
25 Nov - 26 Nov
Colonial Motel And Spa

The Covered Bridge Inn

2.5 star property
8.0 out of 10, Very good, (1000)
"The housekeeping services were excellent and the staff was friendly The facility is a bit old but incredibly clean "
The price is S$108
includes taxes & fees
1 Dec - 2 Dec
The Covered Bridge Inn

Hampton Inn Brattleboro

2.5 star property
8.4 out of 10, Very good, (1009)
"Easiet and nicest place ive stayed in a while"
The price is S$144
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Brattleboro
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Brattleboro?

Yes, there are holiday rentals in Brattleboro close to Brattleboro Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and ski slopes in Brattleboro. Leave some time to check out the shops and entertainment venues during your trip.

How many holiday rentals are there in Brattleboro?

Expedia has 16 holiday rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Connecticut River, or simply take in cultural attractions like The Stone Church and Tasha Tudor Museum. Other places in town to visit include Latchis Theatre and Brattleboro Bowl.

What’s a holiday rental in Brattleboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brattleboro. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.