Vacation rentals in Brattleboro

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Popular amenities for Brattleboro vacation rentals

Stay near Brattleboro's top sights

Whetstone Station Restaurant and Brewery113 locals recommend
The Vermont Country Deli29 locals recommend
99 Restaurants7 locals recommend
Chelsea Royal Diner31 locals recommend
Hannaford Supermarket43 locals recommend
Ramunto's Brick Oven Pizza3 locals recommend

Pet-friendly vacation rentals in Brattleboro

Guest favorite
Tiny home in Wardsboro
4.94 out of 5 average rating, 324 reviews

Little Red House Vermont

JorgeRating, 5 stars1 month ago
What an amazing place to visit Vermont. I had a great time at the little red house. The place is beautiful and quiet. It is a 12 min drive to Mount Snow. Joe has a bunch of classic DVDs and we enjoyed some of them during our stay. The place is very clean and there is warm water and WiFi.
Top guest favorite
Guesthouse in Stephentown
5 out of 5 average rating, 409 reviews

Dog Friendly Studio

AbbyRating, 5 stars4 days ago
Our stay at Maple Hill Farm was so peaceful and exactly what we wanted. We loved being amongst the animals and nature and it was such an incredible hidden gem that we will think about for a long time after our trip has finished. Philip was an incredible host and we loved meeting his sweet pups too. Can’t wait to come back again!
Top guest favorite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Top guest favorite
Chalet in Dover
4.98 out of 5 average rating, 109 reviews

Mountain Chalet: Brook-Hot Tub-Firepit-Mins to Ski

EricRating, 5 stars1 month ago
Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.
Guest favorite
Apartment in Keene
4.94 out of 5 average rating, 218 reviews

The Carriage House Loft: Seasonal Stays

LakeRating, 5 stars3 weeks ago
This property is a very welcome getaway and we felt right at home. Thanks again! I'll be back again. 👍
Guest favorite
Cabin in Danby
4.89 out of 5 average rating, 295 reviews

April/May special So Vt Cabin Mt Tabor Treasure

FavyanRating, 5 stars1 month ago
Second time staying here to hike the area trails. The place was immaculate as was my first visit. The hosts are wonderful and helpful. They gave me check in flexibility that added a lot of time to my plans for the day that ended up being a big value. Highly recommend.
Guest favorite
Barn in Newfane
4.97 out of 5 average rating, 150 reviews

Beautiful rustic woods and fields retreat.

AmberRating, 5 stars1 month ago
This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!
Guest favorite
Cabin in Wells
4.94 out of 5 average rating, 192 reviews

Gatsby's Getaway

MariellaRating, 5 stars1 month ago
The name doesn’t lie; staying here was truly a getaway for my partner and I who wanted some time away from our usual city life. The space was equally as clean as it was cozy, and the view from the back porch is beautiful. Thank you Kiki for a great stay!

Boutique hotels in Brattleboro

Guest favorite
Hotel room in Keene
4.95 out of 5 average rating, 38 reviews

Burrell House Inn, historic Keene NH-" Ivory Room"

JosephRating, 5 stars3 days ago
This was our 3rd time staying here. We have been in three different rooms they have all been great. Last time we had left something in the room they called us within 30 mins of checking out and I was able to go back and get it. Their prices are clear and extremely reasonable for the accommodations and the location. Our daughter is a senior at Keene State College so it has been 4 years of knowing they are there when we need to stay. The rooms are always clean and neat. They are not over burdened with furniture. The rooms are up to date yet also match the area and home. They have a very quaint vibe. Parking is not an issue as they have plenty of it out back. Even when our daughter graduates in May we sill still go back to see her friends next year and the Burrell house will definitely be an option for us. The only thing I would say is the WIFI could use a boost. I was able to use it but only on one side of the room. We would definitely stay there again and recommend it highly.
Superhost
Hotel room in Goshen
4.71 out of 5 average rating, 28 reviews

Victorian Rose Room; Historic Brook Rd Inn

GabrielRating, 5 stars12 months ago
Great place to crash at an affordable price!
Hotel room in Lenox
5 out of 5 average rating, 5 reviews

★ Romantic King Room w/ Double Jacuzzi & Fireplace

AmandaRating, 5 stars25 months ago
Stan made sure we had information on all of the local restaurants, which was super helpful! The hot tub was wonderful, clean, and was perfect for the two of us to enjoy comfortably. Check in was easy and the room was very comfortable. We would happily return!
Superhost
Hotel room in Dover
5 out of 5 average rating, 7 reviews

Luxury King Suite w/balcony in Historic Inn, rm 1

SamirRating, 5 stars27 months ago
Location to Mt Snow was perfect. Amenities were great. Will be back for sure. Very good and welcoming staff that made you feel at ease and comfortable as you’re home.
Superhost
Hotel room in Sunapee
4.89 out of 5 average rating, 45 reviews

Studio Suite #2 at The Lodge | Minutes from Sunape

TiaraRating, 5 stars3 months ago
We stayed at Caitlin’s place for a ski weekend and loved our stay! It was so close to Sunapee Mt., which was great! Also, the location and Airbnb were both beautiful. The place was super clean and the perfect size. It had everything we needed for a weekend away. We would for sure stay here again!
Hotel room in Lenox
4.63 out of 5 average rating, 8 reviews

Constance Double Queen Suite

HannahRating, 5 stars15 months ago
This is my favorite place to stay in the Berkshires after many years of visiting the area. It is even better than the website shows, for personal touches like the common living room area with chess set and piano and cozy window seat nook. It also has amenities like access to beverages and snacks 24 hours/day in the common dining room, lovely views from the rooms and common areas, friendly and competent staff, beautiful furnishings, reliable heat, clean linens, and overall pleasant atmosphere. Plenty of parking, walkable to Lenox, short drive to Tanglewood and Kripalu and other sites. I could not recommend more highly!
Hotel room in Manchester
4.75 out of 5 average rating, 52 reviews

Aspen Manchester, Equinox Suite

AndrewRating, 5 stars27 months ago
The Aspen at Manchester was clean and easy to check into. A great place to relax and unwind after skiing at Stratton. Town of Manchester has plenty of delicious places to grab a bite and its only about 25 minutes from the Stratton resort. Would absolutely stay here again!
Guest favorite
Hotel room in Sunapee
5 out of 5 average rating, 26 reviews

Studio Suite at The Lodge | Walk to Sunapee Harbor

AndreRating, 5 stars2 months ago
Caitlin’s space was great. There were great views and it was a quiet location.

Pet-friendly boutique hotels in Brattleboro

Superhost
Hotel room in Bennington
4.9 out of 5 average rating, 71 reviews

Harwood Hill Motel - Cottages Queen+Twin Sofabed

Edward & ColleenRating, 5 stars5 months ago
Easy to find and nice location. A great local restaurant is walking distance to the hotel. Clean room.
Guest favorite
Hotel room in Bennington
5 out of 5 average rating, 17 reviews

Harwood Hill Motel - Deluxe King

ErinRating, 5 stars4 months ago
Very cute place. Offered contactless check in. The lights in the room were on when we arrived at night. Easy parking, very clean and the bed was very comfortable. Will definitely stay again.
Superhost
Hotel room in Bennington
4.92 out of 5 average rating, 52 reviews

Harwood Hill Motel - Deluxe Queen

JacobRating, 5 stars13 months ago
Great place to stay when I arrived late in Vermont after many hours of driving through. Torrential rain. Martha was a nice host. Not sure why she cared that. I was a last minute guest, however. It’s a Hotel. People show up last minute.
Superhost
Hotel room in Cummington
4.82 out of 5 average rating, 85 reviews

Singing Bridge Harmony Room

EileenRating, 5 stars2 months ago
Wonderful place perfect for our weekend get away with our “ fur baby” felt very welcoming
Guest favorite
Hotel room in Sunapee
4.96 out of 5 average rating, 27 reviews

1 Bed/1.5 Bath Suite #10 The Lodge, Mountain Views

ChristopherRating, 5 stars2 months ago
Perfect place to stay! Would definitely recommend.
Superhost
Hotel room in Bennington
4.89 out of 5 average rating, 71 reviews

Harwood Hill Motel - Economy Queen

ChrisRating, 5 stars20 months ago
Martha was a great host! Very prompt communication and pleasant to work with.
Hotel room in Lenox
4.72 out of 5 average rating, 86 reviews

Standard Two Double in Boutique Lenox Hotel

SahianRating, 5 stars1 month ago
Great hotel, the check in was really fast even though I got there after hours the instructions were clear.
Hotel room in Dover
4.7 out of 5 average rating, 20 reviews

Standard King at Boutique Hotel in Vermont

SarahRating, 5 stars12 months ago
This place is great! The inn itself is clean and safe and it is right across the street from the mountain! You can also take a free shuttle!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Brattleboro