Holiday Homes in Brattleboro

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Find holiday rentals that suit your style

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Cabins
Cabins
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Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Brattleboro holiday homes

A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is AU$140
includes taxes & fees
30 Nov - 1 Dec
Cozy Vermont Tiny Home Get Away
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

2. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 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 AU$567
includes taxes & fees
18 Nov - 19 Nov
Stunning Glass House nestled in the Vermont wilderness!
A garden with a wooden pergola, purple flowers, and a river view.

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (66 reviews)
"Had a perfect, relaxing stay in this gorgeous spot. Everything was terrific. Highly recommend!"
United States
Wendy B.
The price is AU$408
includes taxes & fees
17 Nov - 18 Nov
Family Friendly Hilltop House In Putney Vermont
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

4. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (7 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$170
includes taxes & fees
12 Nov - 13 Nov
The Eagles Wing at The CHM - Private Apartment
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

5. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (74 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is AU$350
includes taxes & fees
19 Nov - 20 Nov
Lovely 2nd Floor Apartment
A rural landscape with a house surrounded by autumn foliage and a river.

6. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$850
includes taxes & fees
12 Nov - 13 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is AU$290
includes taxes & fees
12 Nov - 13 Nov
Private room with En-suite bathroom Marigold Room
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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 AU$659
includes taxes & fees
12 Nov - 13 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (28 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AU$511
includes taxes & fees
18 Nov - 19 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A house with a garage, surrounded by snow-covered trees and a mountain in the background.

10. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Very peaceful backyard!! Great back deck!!"
United States
Jacqueline M.
The price is AU$690
includes taxes & fees
12 Nov - 13 Nov
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
A wooden barrel structure with a staircase and railing, surrounded by a forest.

11. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is AU$864
includes taxes & fees
16 Nov - 17 Nov
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

12. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is AU$379
includes taxes & fees
12 Nov - 13 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts
A hallway with wooden flooring, white walls, and a bed in the background.

13. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is AU$564
includes taxes & fees
12 Nov - 13 Nov
Shelburne Falls on Main
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

14. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is AU$742
includes taxes & fees
12 Nov - 13 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

15. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AU$753
includes taxes & fees
16 Nov - 17 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious living area with a fireplace, a sofa, and a dining table.

16. Mount Snow Cabin • Fireplace • Fire Pit • Pet Friendly • Sleeps 8

Mount Snow Cabin • Fireplace • Fire Pit • Pet Friendly • Sleeps 8
Dover
10.0 out of 10, Exceptional, (6 reviews)
"The house was in perfect condition, extremely clean, thoughtfully stocked with everything we could need and Lisa was most helpful, informative and we look forward to staying there again. "
United States
Alan H.
The price is AU$1,123
includes taxes & fees
28 Nov - 29 Nov
Mount Snow Cabin • Fireplace • Fire Pit • Pet Friendly • Sleeps 8
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

17. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is AU$927
includes taxes & fees
15 Nov - 16 Nov
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

18. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
Walk To Town, Hottub, Firepit, Games, Mt Snow
A pathway through a forest with autumn leaves and a wooden bridge.

19. Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic

Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Great location! The host was fantastic and made our stay so convenient. Highly recommend!"
United States
Allison H.
The price is AU$918
includes taxes & fees
17 Nov - 18 Nov
Book the Lemondrop for your Thanksgiving and experience Vermont’s Fall Magic
A two-story house with a porch, surrounded by trees and snow.

20. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 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 AU$411
includes taxes & fees
12 Nov - 13 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT 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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Learn more about Brattleboro

This artsy riverside town charms visitors with its vibrant city centre galleries and the famous Vermont Farmers Market. Hike the nearby trails for stunning Connecticut River views, then browse independent bookshops and catch live music at local venues.

See all hotels in Brattleboro
A river with a bridge, a town, and surrounding hills.

Top reviews in Brattleboro

A dock extending into a lake with a grassy area in the foreground and trees in the background.
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield

8/10 Good

Pleasant stay hotel was empty when we arrived but filled up a bit by evening.
Australia
Jen123
Reviewed August 30, 2014
Riverside Hotel, an Ascend Collection Hotel