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Compare 508 Vacation Homes in Brattleboro with updated reviews, rates, and availability.

Plenty of Room For Everyone! - 5 Minutes to Stratton
Fire Pit - Front Yard
Plenty of Room For Everyone! - 5 Minutes to Stratton
9.8 out of 10, Exceptional, (10)
"We had a great time staying here! It was close to the Stratton Mountain Resort to go see the foliage, a few cute cafes nearby for coffee and food, and the house itself was comfortable. Beautiful little porch balcony and functioning grill."
The price is SAR 943
SAR 3,374 total
includes taxes & fees
11 Nov - 12 Nov
Plenty of Room For Everyone! - 5 Minutes to Stratton
Cozy, charming mountain home.
Room
Cozy, charming mountain home.
9.8 out of 10, Exceptional, (6)
"Wonderful place to eacape to relax. "
Cozy, charming mountain home.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (15)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (40)
"We stayed at Chris' mansion for my wedding this past weekend and it was everything I expected and more. Although it isn't a full service venue, the owner Chris was sooooo helpful in getting everything we needed for our wedding. He owns a restaurant as well and was able to provide all of our appetizers, servers and bartenders! We even had our rehearsal dinner at his bar down the street called Jax on Tap. The bartenders were absolutely amazing and made us feel so welcome. They even made a sign...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
Living area
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
10.0 out of 10, Exceptional, (12)
"This house was great! It was very clean, had lots of bedrooms, and plenty of room for our group of 7 to have a great weekend. The host was super nice and responded quickly to messages. I would note that there are a lot of stairs, both to get into the house and within the house. Probably not a big deal for people who stay for skiing, but good to know if you have older guests or people who have trouble with stairs."
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Stratton Vacation Rental | 3BR | 2.5BA | 1,600 Sq Ft | Stairs Required
Sunny Stratton Townhome ~ 1 Mi to Skiing!
10.0 out of 10, Exceptional, (4)
"Wonderful and clean townhome! Perfect location to be close to Stratton Resort. Thank you!"
Sunny Stratton Townhome ~ 1 Mi to Skiing!
New Chalet mins to Mt with Hot tub
Newly constructed cottage minutes from the mountain
New Chalet mins to Mt with Hot tub
10.0 out of 10, Exceptional, (2)
"Excellent house, very beautiful, very spacious and much better than what is seen in the photos 10 out of 10 I loved it, without a doubt I would return to this place with my family"
New Chalet mins to Mt with Hot tub
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Vacation Rental | 3BR | 3.5BA | Steps to Enter | 1,750 Sq Ft
Walk to Ski Lift: Spacious Condo in West Dover!
2.0 star property
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Townhome Near Mount Snow Shuttle Stop!
West Dover Vacation Rental | 4BR | 3.5BA | 1,800 Sq Ft | Stairs to Access
West Dover Townhome Near Mount Snow Shuttle Stop!
2.0 star property
West Dover Townhome Near Mount Snow Shuttle Stop!
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
7.8 out of 10, Good, (41)
"Can't beat the location. We had a great stay."
The price is SAR 278
SAR 1,014 total
includes taxes & fees
6 Nov - 7 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Outdoor spa tub
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
10.0 out of 10, Exceptional, (39)
"We had a group of nine and had a great time. There are so many wonderful features including a fully stocked kitchen, activities for kids and an awesome outdoor area to hang out and relax. Would highly recommend this house. "
The price is SAR 999
SAR 2,695 total
includes taxes & fees
12 Nov - 13 Nov
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
House Front. Covered Porches, Lots of sunshine Plenty of space.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (209)
"Clean and well supplied with fantastic views and close proximity to town.....a wonderful fall New England experience! "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Interior
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is SAR 2,062
SAR 4,974 total
includes taxes & fees
24 Nov - 25 Nov
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Exterior
Shuttle or walk to village and lifts! The Powder Haus Chalet!
10.0 out of 10, Exceptional, (31)
"Our group of 8 found the property to be a perfect accomodation while staying in town for a wedding. Check in was very convenient and communication with the host was excellent. The home was very spacious, the living area was a great space to hang out and spend time together. We had all the amenities we needed for an easy weekend while attending a friend's wedding. The location is excellent and was very convenient to the mountain. We are especially grateful for the host allowing our furry friends...
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Take in stunning views from our large windows while cozied by the fire
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
9.0 out of 10, Wonderful, (66)
"We loved it and plan to return some day."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
Property grounds
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
10.0 out of 10, Exceptional, (15)
"Great home in a peaceful location in the country. The place is perfect for a couple and has a cool basement living space."
The price is SAR 1,315
SAR 1,670 total
includes taxes & fees
6 Nov - 7 Nov
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
10.0 out of 10, Exceptional, (43)
"Brad was a wonderful host and the home and area had so much for us to do. It was the perfect place to get away and be with friends. "
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
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

Cozy Cottage Along Idyllic Green River
Green River Cottage
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (42)
"A bit off the beaten path…but worth it! Such an immaculate, comfortable home. It is nestled within the gorgeous beauty of southern Vermont. You can be in Brattleboro for necessities in 20 minutes. There are so many wonderful walks you can take right outside your door. This was just the calm we needed toward the end of our 10 day trip. I would return in a heartbeat!"
Cozy Cottage Along Idyllic Green River
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Exterior detail
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
10.0 out of 10, Exceptional, (12)
"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Dummerston Vacation Rental | 2BR | 1BA | 850 Sq Ft | Steps Required
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (8)
"Cabin was perfect for a weekend getaway. Check in was a breeze and they had a very generous check in check out time which I appreciated. It was on a quiet dead-end street so no through traffic and the sound of the brook was calming. The beds were comfortable. It's not that far of a walk from the parking to the house. Happy we could bring our dogs as well. Short drive to town. Love the Vegan Restaurant in Brattleboro the food was delicious. We hiked a few trails that were nearby. Wish we had...
Cozy Falls Brook Cabin: Hike & Swim On-Site!
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.