Photo by Shirley Rhodes

Holiday Rentals in Brattleboro

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Brattleboro

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat

Cozy Falls Brook Cabin: Hike & Swim On-Site!

10.0 out of 10, Exceptional, (10)
"The cabin is immaculate and very cute and cozy. It's lovely to be right by the brook in a quiet neighborhood set in a woodsy area. Lots of great places a short right away too. Brattleboro is lots of fun, and we loved hiking in the Manitou Project."
Cozy Falls Brook Cabin: Hike & Swim On-Site!

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!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is €386
includes taxes & fees
7 Jan - 8 Jan 2025
Long Trail House at Stratton Mountain Resort

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (151)
"Never could get the wifi to work. I entered the code on the router 6 times but no luck. Would be helpful if you changed the password for the wifi to an easily entered name. The man who came to shovel unfortunately after we were stuck in the snow was very helpful and very nice.. He got us out."
The price is €359
includes taxes & fees
6 Jan - 7 Jan 2025
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Dog-friendly chalet cabin with valley view, deck, and private hot tub

7.6 out of 10, Good, (19)
"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (42)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.6 out of 10, Excellent, (20)
"Wonderful stay. Thanks again"
The price is €538
includes taxes & fees
16 Jan - 17 Jan 2025
Lovely ski-in/out condo steps from ski lift with trails and amazing views

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (9)
"We had a great time staying in Ashley’s condo! It was clean and well kept and super close to the village and slopes. I will definitely be back soon :)"
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (19)
"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (21)
"Good Condo in a great location"
The price is €426
includes taxes & fees
16 Jan - 17 Jan 2025
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (30)
"Cozy 1 bdrm very close to the slopes. The host are vey cooperative abd get back to you quickly."
Walk to Mount Snow, Cozy, Clean and Comfortable!

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (40)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

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 €1,624
includes taxes & fees
20 Jan - 21 Jan 2025
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is €586
includes taxes & fees
3 Jan - 4 Jan 2025
Bear Creek Cabin

Green Mountain Modern House: iconic modern getaway

Green Mountain Modern House: iconic modern getaway

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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.
Don't see what you're looking for?
See all available properties in Brattleboro
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Brattleboro you may be interested in

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Like size of room"
The price is €93
includes taxes & fees
9 Jan - 10 Jan 2025
Colonial Motel And Spa

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1000)
"The front desk staff were great! Free breakfast was ok and one staff Eleanor was excellent. She was friendly, nice, and a professional. She is an asset! The room had comfortable beds, the refrigerator and microwave was a plus! The only issue was that there was no room service and bedsheets were never changed for the duration of our stay. I had to ask for towels, and had the garbage emptied. Eleanor was the only person who vacuumed, cleaned the bathroom, and emptied the garbage when I requested....
The price is €108
includes taxes & fees
12 Jan - 13 Jan 2025
Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (545)
"This place is a gem for the price and convenience to I-91. We got very lucky to find it. There’s a lovely restaurant just across the parking lot, a warm and clean pool, hot soup, hot chocolate, and coffee in the reception area and excellent hospitality. "
The price is €109
includes taxes & fees
12 Jan - 13 Jan 2025
Comfort Inn & Suites Brattleboro I-91
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.

Frequently asked questions

Are there holiday rentals in Brattleboro?

Yes, there are holiday rentals in Brattleboro close to Brattleboro Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and ski slopes in Brattleboro. Leave some time to check out the shops and entertainment venues during your trip.

What are some of the best holiday rentals that Brattleboro has to offer?

The Jelly Mill-A River Retreat: This highly rated holiday home rental in Brattleboro is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Brattleboro?

Expedia has 17 holiday rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Hogback Mountain Conservation Area, or simply take in cultural attractions like Brattleboro Museum & Art Center and The Stone Church. Other places in town to visit include Latchis Theatre and Brattleboro Bowl.

What’s a holiday rental in Brattleboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brattleboro. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.