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Compare 635 Vacation Homes in Brattleboro with updated reviews, rates, and availability.

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,300
AED 2,152 total
includes taxes & fees
12 May - 13 May
Cozy Home Near Downtown, Shops, and Restaurants.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"House was great. We were able to walk up the road with our skis and drop right in. I’d definitely stay here again."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (73)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Potter's Place | House in Jamaica with mountain views

9.6 out of 10, Exceptional, (4)
"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"
Potter's Place | House in Jamaica with mountain views

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"This is one of the nicest places our family has ever stayed at. We have been skiing for at least 35 years at many different locations and this place is beautiful. Very accessible to the mountain. Todd is very easy to communicate with and answers any questions you may have right away. Plenty of room for our whole family of all ages. We will be coming back next ski season. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Cozy retreat near slopes

5.0 out of 10, (8)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "
The price is AED 716
AED 1,251 total
includes taxes & fees
11 May - 12 May
Family Friendly Hilltop House In Putney Vermont

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

10.0 out of 10, Exceptional, (2)
"Beautiful house well stocked with spices and everything you need. The only thing they are missing is there’s no hairdryer and I called a few times to the property manager for a blanket because the master upstairs has no blanket and I never received one."
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

10.0 out of 10, Exceptional, (1)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (19)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (68)
"Several items, microwave and dishwasher, were not working. House was somewhat clean. Great location, but very dated and in need of a upgrade."
Mountain-view home near the slopes with at-home entertainment - dog-friendly

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (15)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

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

7.8 out of 10, Good, (46)
"Can't beat the location. We had a great stay."
The price is AED 261
AED 935 total
includes taxes & fees
11 May - 12 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (22)
"Place was great and accommodating, would recommend. Thank you!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (217)
"The owner was available through call/text, although we didn’t need anything. Beautiful house with even more beautiful views. The game room was a big hit. Hot tub and sauna were great as well. This house has everything! We will definitely be back!"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"great Place, quiet, clean and very comfortable."
The price is AED 404
AED 1,569 total
includes taxes & fees
11 May - 12 May
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

10.0 out of 10, Exceptional, (19)
"Great location directly across from Mount Snow great place, clean, all amenities, definitely will return "
The price is AED 588
AED 1,685 total
includes taxes & fees
11 May - 12 May
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge
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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Other property types in Brattleboro

Hike & Swim On-Site: Cozy Falls Brook Cabin

10.0 out of 10, Exceptional, (10)
"Great little cabin, would definitely stay again!"
Hike & Swim On-Site: Cozy Falls Brook Cabin

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AED 624
AED 1,345 total
includes taxes & fees
12 May - 13 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.