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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Brattleboro holiday homes

A bathroom with a white toilet, a mirror, and a towel rack.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is €97
includes taxes & fees
17 Nov - 18 Nov
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 €451
includes taxes & fees
8 Nov - 9 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, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is €254
includes taxes & fees
26 Oct - 27 Oct
Family Friendly Hilltop House In Putney Vermont
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is €230
includes taxes & fees
5 Nov - 6 Nov
Lovely 2nd Floor Apartment
A white sign with the word 'ENTRANCE' hanging from a black metal bracket against a white wall.

5. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is €182
includes taxes & fees
26 Oct - 27 Oct
The Eagles Wing at The CHM - Private Apartment
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

6. 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, (4 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 €436
includes taxes & fees
27 Oct - 28 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is €572
includes taxes & fees
26 Oct - 27 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

8. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is €323
includes taxes & fees
29 Oct - 30 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

9. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is €188
includes taxes & fees
15 Nov - 16 Nov
Private room with En-suite bathroom Marigold Room
A cozy living room with a beige sofa, a wooden coffee table, and two lamps.

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, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is €434
includes taxes & fees
27 Oct - 28 Oct
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 €606
includes taxes & fees
1 Nov - 2 Nov
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
A hallway with wooden flooring, white walls, and a bed in the background.

12. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
"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 €368
includes taxes & fees
2 Nov - 3 Nov
Shelburne Falls on Main
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.

13. 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 €369
includes taxes & fees
26 Oct - 27 Oct
Modern Mount Snow Gnarvana - Steps to Carinthia
A spacious kitchen with wooden flooring, a central island with stools, a dining table, and pendant lighting.

14. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 reviews)
"This home was comfy, really clean and hosts were easy to reach and chat with during our stay. My extended family had a great time getting together this summer staying at hosts’ home!"
United States
Griffin S.
The price is €585
includes taxes & fees
25 Oct - 26 Oct
Spacious 5BR w/ Hot Tub & Games
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 €514
includes taxes & fees
25 Oct - 26 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

16. 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 €237
includes taxes & fees
25 Oct - 26 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

17. 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.
The price is €705
includes taxes & fees
25 Oct - 26 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A bedroom with a bed, bedside tables, a window, and a radiator.

18. 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 €359
includes taxes & fees
27 Oct - 28 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

19. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is €612
includes taxes & fees
27 Oct - 28 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

20. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is €1,046
includes taxes & fees
23 Oct - 24 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
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

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent
"Clean room, but very old and needs updating. TV had Netflix and Prime."
Nazia 2-night trip
Posted 14 hours ago
Travelodge by Wyndham Brattleboro VT

Find out more about Brattleboro

Brattleboro Holiday Homes information

Number of reviews
429
Accommodation
571 Holiday Homes
Lowest Price
€97
Highest Price
€1,046