A calm lake reflecting a forest with autumn foliage.

Holiday Homes in Brattleboro

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Brattleboro holiday homes

Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
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 NZ$814
includes taxes & fees
6 July - 7 July
Stunning Glass House nestled in the Vermont wilderness!
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (58 reviews)
"Very clean and cozy apartment. "
United States
Kim G.
The price is NZ$361
includes taxes & fees
30 June - 1 July
Lovely 2nd Floor Apartment
Interior

Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
The price is NZ$646
includes taxes & fees
30 June - 1 July
Shelburne Falls on Main
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
Private bed with En-suite bathroom Marigold Room
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is NZ$562
includes taxes & fees
1 July - 2 July
Family Friendly Hilltop House In Putney Vermont
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is NZ$634
includes taxes & fees
2 July - 3 July
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is NZ$774
includes taxes & fees
30 June - 1 July
The Greylock Cabin
Interior

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is NZ$452
includes taxes & fees
30 June - 1 July
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at a great ski house that was in a good location to the mountain. Accommodations were comfortable for 6 adults and 4 kids and the shuffleboard, foosball and pool tables were a hit. "
United States
Jonathan H.
The price is NZ$1,417
includes taxes & fees
30 June - 1 July
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 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 NZ$1,218
includes taxes & fees
30 June - 1 July
5BR Berkshire Home Mins To The Mountain
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is NZ$760
includes taxes & fees
2 July - 3 July
Two Brooks Lodge
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is NZ$1,724
includes taxes & fees
21 July - 22 July
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Interior

Private Cabin 4BR/3BA Fire pit, Pool table, BBQ Weber Grill, Bubbling Brook

Private Cabin 4BR/3BA Fire pit, Pool table, BBQ Weber Grill, Bubbling Brook
Dover
The price is NZ$915
includes taxes & fees
30 June - 1 July
Private Cabin 4BR/3BA Fire pit, Pool table, BBQ Weber Grill, Bubbling Brook
Exterior

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.

Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Jamaica
8.8 out of 10, Excellent, (8 reviews)
"Beautiful home, we enjoyed our stay!"
United States
Luke B.
The price is NZ$1,246
includes taxes & fees
30 June - 1 July
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
Exterior

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
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 NZ$975
includes taxes & fees
15 July - 16 July
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Terrace/patio

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is NZ$1,200
includes taxes & fees
30 June - 1 July
3 Mi to Mount Snow: Spacious West Dover Home
Dining

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (18 reviews)
"Great place!"
United States
Jack & Heather G.
The price is NZ$1,085
includes taxes & fees
22 July - 23 July
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is NZ$852
includes taxes & fees
30 July - 31 July
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (50 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is NZ$1,079
includes taxes & fees
26 July - 27 July
Spacious 5BR w/ Hot Tub & Games
Fridge, microwave, oven, stovetop

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is NZ$1,006
includes taxes & fees
22 July - 23 July
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Awesome"
Kevin 1-night trip
Posted 5 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Brattleboro

Brattleboro Holiday Homes information

Number of reviews
318
Accommodation
543 Holiday Homes
Lowest Price
NZ$361
Highest Price
NZ$1,724