Brattleboro Holiday Rentals

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Our top choices for Brattleboro holiday rentals

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is NZ$347
includes taxes & fees
24 Feb - 25 Feb
Vikings Villages Resort - Double Bed Room

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is NZ$432
includes taxes & fees
20 Feb - 21 Feb
The Studio with a View. Bring your dog, too!

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is NZ$694
includes taxes & fees
18 Feb - 19 Feb
Stunning Glass House nestled in the Vermont wilderness!

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (17 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
The price is NZ$558
includes taxes & fees
25 Feb - 26 Feb
Owl's Nest Treehouse

Ski on ski off condo

Ski on ski off condo
Stratton
9.8 out of 10, Exceptional, (74 reviews)
"Joe was very accommodating with my short notice reservation. Great spot, very spacious! "
United States
Thomas M.
The price is NZ$2,173
includes taxes & fees
13 Feb - 14 Feb
Ski on ski off condo

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is NZ$498
includes taxes & fees
24 Feb - 25 Feb
Lake Whitingham & Mount Snow Area Village Apartment

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is NZ$865
includes taxes & fees
2 Mar - 3 Mar
Long Trail House at Stratton Mountain Resort

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (48 reviews)
"Very cute apartment, clean and nice furnishings, bed was very comfortable."
United States
Matthew H.
The price is NZ$333
includes taxes & fees
13 Feb - 14 Feb
Lovely 2nd Floor Apartment

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, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is NZ$1,090
includes taxes & fees
23 Feb - 24 Feb
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (166 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is NZ$602
includes taxes & fees
25 Feb - 26 Feb
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Modern 6BR Home for Large Groups & Families

Modern 6BR Home for Large Groups & Families
Keene
The price is NZ$1,310
includes taxes & fees
20 Feb - 21 Feb
Modern 6BR Home for Large Groups & Families

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful view, very spacious outside and indoors, cozy aesthetic."
United States
Devon I.
The price is NZ$981
includes taxes & fees
22 Feb - 23 Feb
Bear Creek Cabin

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!
Marlborough
The price is NZ$583
includes taxes & fees
24 Feb - 25 Feb
Large 3BR Apartment in Marlborough NH: Sleeps 8-10: Close to Keene!

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is NZ$483
includes taxes & fees
18 Feb - 19 Feb
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (1 review)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is NZ$770
includes taxes & fees
13 Feb - 14 Feb
Terrific 3-bedroom unit in charming Leverett with AC

Free HOT Breakfast for each guest everyday! Located in charming Whitingham

Free HOT Breakfast for each guest everyday! Located in charming Whitingham
Whitingham
The price is NZ$1,043
includes taxes & fees
16 Feb - 17 Feb
Free HOT Breakfast for each guest everyday! Located in charming Whitingham

5 Mi to Mt Snow: Secluded Family Home w/ Game Area

5 Mi to Mt Snow: Secluded Family Home w/ Game Area
3.0 star property
West Dover
5 Mi to Mt Snow: Secluded Family Home w/ Game Area

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful neighborhood to take walks. Home was very clean, as you see in the photo. Very spacious and relaxing. Pretty home overall."
United States
Stephen G.
The price is NZ$2,519
includes taxes & fees
9 Mar - 10 Mar
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Luxury ADA Unit - 101

Luxury ADA Unit - 101
Wilmington
10.0 out of 10, Exceptional, (1 review)
"It was a beautiful place and clean and updated. Plenty of room for our party of four."
United States
Michael
The price is NZ$1,009
includes taxes & fees
22 Feb - 23 Feb
Luxury ADA Unit - 101

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is NZ$1,007
includes taxes & fees
3 Mar - 4 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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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Find out more about Brattleboro

Everything you need to know about Brattleboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Brattleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brattleboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brattleboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brattleboro holiday rentals we have selected for you start as low as NZ$520 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Brattleboro rentals

At Expedia, we put the best Brattleboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Brattleboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brattleboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brattleboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Brattleboro is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Brattleboro?

Expedia has 23 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 The Stone Church and Hooker-Dunham Theater & Gallery. Other places in town to visit include Latchis Theatre and Harris Hill Ski Jump.

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.