A calm lake reflecting a forest with autumn foliage.

Brattleboro Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Brattleboro holiday rentals

Private kitchen

1. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is HK$890
HK$1,946 total
includes taxes & fees
2 Sept - 3 Sept
The Studio with a View. Bring your dog, too!
Living area

2. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is HK$1,229
HK$3,477 total
includes taxes & fees
7 Sept - 8 Sept
Stunning Glass House nestled in the Vermont wilderness!
Terrace/patio

3. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,158
HK$2,678 total
includes taxes & fees
25 Aug - 26 Aug
Vikings Villages Resort - Double Bed Room
Property grounds

4. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is HK$579
HK$1,054 total
includes taxes & fees
25 Aug - 26 Aug
Yurt Oasis in the woods of Hinsdale, NH
Terrace/patio

5. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is HK$706
HK$1,235 total
includes taxes & fees
24 Aug - 25 Aug
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Exterior

6. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,012
HK$3,589 total
includes taxes & fees
1 Sept - 2 Sept
Chalet Mount Snow/Stratton Skiing/hiking
Interior

7. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is HK$911
HK$1,605 total
includes taxes & fees
26 Aug - 27 Aug
Lovely 2nd Floor Apartment
Outdoor dining

8. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$432
HK$639 total
includes taxes & fees
16 Aug - 17 Aug
2 private mountain RV pads for rent. Full hook ups
Outdoor pool, a heated pool

9. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$534
HK$2,492 total
includes taxes & fees
31 Aug - 1 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

10. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,370
HK$2,510 total
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Beach

11. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is HK$636
HK$2,243 total
includes taxes & fees
20 Aug - 21 Aug
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior detail

12. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (9 reviews)
"We had a great"
United States
Meredith B.
The price is HK$946
HK$2,214 total
includes taxes & fees
27 Aug - 28 Aug
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
1 bedroom, desk, iron/ironing board, WiFi

13. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is HK$895
HK$1,639 total
includes taxes & fees
26 Aug - 27 Aug
Balcony Room in Victorian Home private bath
Exterior

14. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (34 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is HK$847
HK$1,485 total
includes taxes & fees
14 Aug - 15 Aug
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Lobby

15. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is HK$824
HK$2,830 total
includes taxes & fees
18 Aug - 19 Aug
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Smart TV, fireplace, Netflix, streaming services

16. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$1,347
HK$3,996 total
includes taxes & fees
1 Sept - 2 Sept
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

17. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (170 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is HK$1,334
HK$2,909 total
includes taxes & fees
17 Aug - 18 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Iron/ironing board, WiFi, bed sheets

18. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is HK$1,263
HK$2,866 total
includes taxes & fees
2 Sept - 3 Sept
Cozy private 2 bed apartment in Shelburne Falls
TV, fireplace

19. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (35 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is HK$585
HK$2,488 total
includes taxes & fees
16 Aug - 17 Aug
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

20. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$942
HK$1,692 total
includes taxes & fees
31 Aug - 1 Sept
Private bed with En-suite bathroom Marigold Room
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 Brattleboro Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The room was clean and quiet and the air conditioning worked well. There is a full breakfast and a nice work out room. This is the second time I have stayed at this Best Western, and I will stay there again the next time I am in Keane NH."
Daniel 1-night trip
Posted 5 hours ago
Best Western Plus Keene Hotel

Find out more about Brattleboro

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

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

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

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.

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

The Jelly Mill-A Peaceful River Retreat: This highly rated holiday home rental in Brattleboro is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Brattleboro?

Expedia has 28 holiday rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Hogback Mountain Conservation Area, or simply take in cultural attractions like The Stone Church and Brattleboro Museum & Art Center. Other places in town to visit include Latchis Theatre and Vermont Marketplace.

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.