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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Brattleboro holiday homes

A room with a red sofa, a wooden table, a vase with flowers, and a window with a view of trees and snow.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is NZ$212
includes taxes & fees
20 Oct - 21 Oct
Cozy Vermont Tiny Home Get Away
A garden with a wooden pergola, purple flowers, and a river view.

2. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 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 NZ$457
includes taxes & fees
20 Oct - 21 Oct
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.

3. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (4 reviews)
"Open modern clean space in a lovely quiet location. The hosts were very responsive and helpful. We would be happy to visit again."
United States
Matthew C.
The price is NZ$247
includes taxes & fees
29 Sept - 30 Sept
The Eagles Wing at The CHM - Private Apartment
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is NZ$402
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is NZ$379
includes taxes & fees
28 Sept - 29 Sept
Private bed with En-suite bathroom Marigold Room
A hallway with wooden flooring, white walls, and a bed in the background.

6. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
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 NZ$753
includes taxes & fees
28 Sept - 29 Sept
Cozy private 2 bed apartment in Shelburne Falls
A dining area with a long table and chairs, large windows with a view of trees, and a barbecue grill outside.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,159
includes taxes & fees
30 Sept - 1 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

8. 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 Sept - 1 Oct
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
An aerial view of a house surrounded by a forest with autumn foliage.

9. 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, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is NZ$926
includes taxes & fees
29 Sept - 30 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

10. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is NZ$1,140
includes taxes & fees
29 Sept - 30 Sept
Spacious 5BR w/ Hot Tub & Games
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

11. 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, (20 reviews)
"Great place!"
United States
Jack & Heather G.
The price is NZ$964
includes taxes & fees
6 Oct - 7 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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.

12. 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 NZ$736
includes taxes & fees
28 Sept - 29 Sept
Modern Mount Snow Gnarvana - Steps to Carinthia
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

13. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (26 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is NZ$648
includes taxes & fees
22 Oct - 23 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

14. 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 NZ$845
includes taxes & fees
20 Oct - 21 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (63 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is NZ$1,328
includes taxes & fees
28 Sept - 29 Sept
Walk To Town, Hottub, Firepit, Games, Mt Snow
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

16. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is NZ$1,111
includes taxes & fees
8 Oct - 9 Oct
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A bedroom with a bed, bedside tables, a window, and a radiator.

17. 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
The price is NZ$758
includes taxes & fees
28 Sept - 29 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

18. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 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$1,160
includes taxes & fees
28 Sept - 29 Sept
5BR Berkshire Home Mins To The Mountain
A two-story house with a porch, surrounded by trees and snow.

19. 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 NZ$553
includes taxes & fees
29 Sept - 30 Sept
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A covered outdoor seating area with a sofa, cushions, a table, and a lantern.

20. Modern 6BR Home for Large Groups & Families

Modern 6BR Home for Large Groups & Families
Keene
8.0 out of 10, Very good, (2 reviews)
"Nice location, with lots of space. Beds were comfy and my shower was nice a warm. Thankyou"
United States
Sheryl M.
The price is NZ$1,358
includes taxes & fees
9 Oct - 10 Oct
Modern 6BR Home for Large Groups & Families
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

Black Mountain Inn

Black Mountain Inn

10/10 Excellent
"Helpful staff, clean room, exactly what we needed for the night."
TIMOTHY 1-night trip
Posted 15 hours ago
Black Mountain Inn

Find out more about Brattleboro

Brattleboro Holiday Homes information

Number of reviews
350
Accommodation
561 Holiday Homes
Lowest Price
NZ$379
Highest Price
NZ$1,358