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Brattleboro Holiday Rentals

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Holiday Rentals in Brattleboro

Stunning Glass House nestled in the Vermont wilderness!

Guilford
10.0 out of 10, Exceptional, (1)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is NZ$721
includes taxes & fees
19 Nov - 20 Nov
Stunning Glass House nestled in the Vermont wilderness!

Vikings Villages Resort - Double Bed Room

Guilford
The price is NZ$650
includes taxes & fees
16 Nov - 17 Nov
Vikings Villages Resort - Double Bed Room

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

Greenfield
10.0 out of 10, Exceptional, (1)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is NZ$365
includes taxes & fees
17 Nov - 18 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Tiny house on the Ashuelot river family and pet friendly

Swanzey
The price is NZ$153
includes taxes & fees
13 Nov - 14 Nov
Tiny house on the Ashuelot river family and pet friendly

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

Dover
9.4 out of 10, Exceptional, (16)
"Extremely clean and lovely place to stay. The area is great, there is a ton to do and see. We went for a hiking trip and enjoyed the places to eat. The one caveat is that it isn't clear in the listing that it's a shared community pool, about a 5 minute walk from the property. It was nicely maintained and really lovely. Biggest downside to our stay was that we were woken up every morning by the children upstairs. "
United States
Rita S.
The price is NZ$447
includes taxes & fees
8 Dec - 9 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (44)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is NZ$356
includes taxes & fees
18 Nov - 19 Nov
Lovely 2nd Floor Apartment

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is NZ$708
includes taxes & fees
13 Nov - 14 Nov
Long Trail House at Stratton Mountain Resort

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Dover
10.0 out of 10, Exceptional, (4)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
The price is NZ$364
includes taxes & fees
30 Nov - 1 Dec
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"Gorgeous property. Super accommodating hosts. Would love to come back in the summer."
United States
Thomas F.
The price is NZ$450
includes taxes & fees
13 Nov - 14 Nov
Family Friendly Hilltop House In Putney Vermont

Wellness Getaway with a Personal Sauna, and Private River Beach!

2.0 star property
Newfane
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is NZ$450
includes taxes & fees
17 Nov - 18 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover
9.0 out of 10, Wonderful, (43)
"We loved the place. It was very homey and comfortable. My only suggestion would be to upgrade the towels and add a few more dish towels. "
United States
Kathy S.
The price is NZ$523
includes taxes & fees
25 Nov - 26 Nov
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford
10.0 out of 10, Exceptional, (27)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is NZ$254
includes taxes & fees
16 Nov - 17 Nov
Getaway Near Mass MoCA, Great Hiking, Scenic Views

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

Dover
8.6 out of 10, Excellent, (31)
"Very nice accommodations and location!"
United States
Michael M.
The price is NZ$498
includes taxes & fees
18 Nov - 19 Nov
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Charming 1-bedroom condo in delightful Dover

Dover
9.6 out of 10, Exceptional, (7)
"Easy to find. Good communication helped, but the sliding door was a little wonky. Additional security for single female travelers would be nice. A bedside table would be useful. All the amenities you would ever need."
United States
Tia
The price is NZ$356
includes taxes & fees
26 Nov - 27 Nov
Charming 1-bedroom condo in delightful Dover

Lake Whitingham & Mount Snow Area Village Apartment

2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is NZ$539
includes taxes & fees
13 Nov - 14 Nov
Lake Whitingham & Mount Snow Area Village Apartment

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

Dover
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is NZ$722
includes taxes & fees
9 Dec - 10 Dec
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls
The price is NZ$310
includes taxes & fees
13 Nov - 14 Nov
2 Twin beds on 1st floor with En-suite bathroom.

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

Stratton
8.4 out of 10, Very good, (26)
"Great location close to lift. Condo is clean and well appointed."
United States
Grace Ann B.
The price is NZ$492
includes taxes & fees
16 Nov - 17 Nov
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton
7.8 out of 10, Good, (52)
"We had a great time at Stratton resort. Suprised my husband with a 9am, 70 min UTV ride up the summit. We were the only ones with our tour guide and had the entire mountain to ourselves. Lily our tour guide was great. She was knowledgeable and informativable."
United States
Diana V.
The price is NZ$437
includes taxes & fees
16 Nov - 17 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole
10.0 out of 10, Exceptional, (8)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
The price is NZ$443
includes taxes & fees
13 Nov - 14 Nov
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to 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.
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Find out more about Brattleboro

Everything you need to know about Brattleboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Brattleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brattleboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brattleboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brattleboro holiday rentals we have selected for you start as low as NZ$492 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Brattleboro rentals

At Expedia, we put the best Brattleboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Brattleboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brattleboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brattleboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 20 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.