Holiday Homes in Brattleboro

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Brattleboro holiday homes

Living area

Holiday Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
10.0 out of 10, Exceptional, (1 review)
"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 €395
includes taxes & fees
31 Mar - 1 Apr
Stunning Glass House nestled in the Vermont wilderness!
Exterior

Holiday Home in Brattleboro

Clean & Convenient - Dogs stay free!
The price is €502
includes taxes & fees
16 Mar - 17 Mar
Clean & Convenient - Dogs stay free!
Interior

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is €174
includes taxes & fees
10 Mar - 11 Mar
Lovely 2nd Floor Apartment
Outdoor spa tub

Holiday Home in Keene

Modern Downtown 12ppl Hot Tub Fire Pit Games
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is €246
includes taxes & fees
9 Mar - 10 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games
Terrace/patio

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is €506
includes taxes & fees
4 Mar - 5 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Dining

Holiday Home in Charlemont

Charlemont Chalet - A 15 Acre Private Retreat
The price is €552
includes taxes & fees
12 Mar - 13 Mar
Charlemont Chalet - A 15 Acre Private Retreat
Exterior

Holiday Home in Whitingham

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is €441
includes taxes & fees
10 Mar - 11 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Fridge, microwave, oven, stovetop

Holiday Home in Colrain

Colrain Spring into Adventure HotTub AirHockey Firepit
9.8 out of 10, Exceptional, (47 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is €547
includes taxes & fees
4 Mar - 5 Mar
Colrain Spring into Adventure HotTub AirHockey Firepit
Interior

Holiday Home in Dover

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is €483
includes taxes & fees
8 Mar - 9 Mar
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
TV

Holiday Home in Florida

Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €293
includes taxes & fees
4 Mar - 5 Mar
Florida Mountain Log Cabin
Property grounds

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €255
includes taxes & fees
1 Apr - 2 Apr
Family Friendly Hilltop House In Putney Vermont
Fridge, microwave, oven, stovetop

Holiday Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
10.0 out of 10, Exceptional, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is €420
includes taxes & fees
12 Mar - 13 Mar
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Fridge, oven, stovetop, dishwasher

Holiday Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is €420
includes taxes & fees
17 Mar - 18 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Interior

Holiday Home in Stratton

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is €246
includes taxes & fees
1 Apr - 2 Apr
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds

Holiday Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is €370
includes taxes & fees
15 Mar - 16 Mar
Riverbend Berkshire East Basecamp - 3 bedrooms available
Smart TV, fireplace, books

Holiday Home in Charlemont

Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
10.0 out of 10, Exceptional, (2 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is €547
includes taxes & fees
4 Mar - 5 Mar
Five Bedroom Berkshire East Basecamp - Winter Vintage Vibe Retreat
Exterior

Holiday Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is €342
includes taxes & fees
5 Mar - 6 Mar
The Greylock Cabin
Fridge, microwave, oven, stovetop

Holiday Home in Dover

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."
United States
Stephen G.
The price is €1,042
includes taxes & fees
1 Apr - 2 Apr
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
TV, books, stereo

Holiday Home in Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views
The price is €442
includes taxes & fees
31 Mar - 1 Apr
Secluded Vermont Chalet w/ Sweeping Mountain Views
Interior

Holiday Home in Wardsboro

Stratton Woods · Secluded Vermont Cabin Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is €351
includes taxes & fees
24 Mar - 25 Mar
Stratton Woods · Secluded Vermont Cabin Retreat
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Shuttle if very efficient and the wait is never long to get to the slopes and village area. Great area for walks and/or with dogs. Although I was hoping for pancakes or waffles with the continental breakfast but was great nonetheless. Had dinner reservations in the village and the shuttle was the way to go on a super cold night. It’s just what you need to be comfortable. Hot tub and sauna was refreshing. I’d would deff recommend staying there again. "
Cherish Kae 1-night trip
Posted 13 hours ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Brattleboro

Brattleboro Holiday Homes information

Number of reviews
337
Accommodation
541 Holiday Homes
Lowest Price
€174
Highest Price
€1,042