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Brattleboro Holiday Rentals

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Holiday Rentals in Brattleboro

Stunning Glass House nestled in the Vermont wilderness!
10.0 out of 10, Exceptional, (1)
"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 AU$659
includes taxes & fees
5 Nov - 6 Nov
Stunning Glass House nestled in the Vermont wilderness!
Vikings Villages Resort - Double Bed Room
The price is AU$573
includes taxes & fees
5 Nov - 6 Nov
Vikings Villages Resort - Double Bed Room
Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is AU$394
includes taxes & fees
28 Oct - 29 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!
Charming 1-bedroom condo in delightful Dover
9.6 out of 10, Exceptional, (7)
"Easy to find. Good communication helped, but the sliding door was a little wonky. Additional security for single female travelers would be nice. A bedside table would be useful. All the amenities you would ever need."
United States
Tia
The price is AU$313
includes taxes & fees
19 Nov - 20 Nov
Charming 1-bedroom condo in delightful Dover
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (41)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is AU$313
includes taxes & fees
29 Oct - 30 Oct
Lovely 2nd Floor Apartment
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
The price is AU$350
includes taxes & fees
3 Nov - 4 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
10.0 out of 10, Exceptional, (4)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
The price is AU$320
includes taxes & fees
31 Oct - 1 Nov
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is AU$396
includes taxes & fees
4 Nov - 5 Nov
Family Friendly Hilltop House In Putney Vermont
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (164)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
United States
Jennifer
The price is AU$549
includes taxes & fees
27 Oct - 28 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Owl's Nest Treehouse
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is AU$522
includes taxes & fees
27 Oct - 28 Oct
Owl's Nest Treehouse
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (75)
"Nice, clean room in prime location"
United States
Kristin
The price is AU$608
includes taxes & fees
30 Oct - 31 Oct
Long Trail House at Stratton Mountain Resort
Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 AU$476
includes taxes & fees
27 Oct - 28 Oct
Lake Whitingham & Mount Snow Area Village Apartment
Florida Mountain Log Cabin!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is AU$690
includes taxes & fees
2 Nov - 3 Nov
Florida Mountain Log Cabin!
Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is AU$567
includes taxes & fees
27 Oct - 28 Oct
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AU$654
includes taxes & fees
2 Nov - 3 Nov
Mountain Chalet mins from Mt Snow Skiing/hiking
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
United States
Evan C.
The price is AU$454
includes taxes & fees
28 Oct - 29 Oct
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is AU$941
includes taxes & fees
2 Nov - 3 Nov
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
The price is AU$664
includes taxes & fees
18 Nov - 19 Nov
Downtown Hot Tub Escape
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
10.0 out of 10, Exceptional, (14)
"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 AU$763
includes taxes & fees
5 Nov - 6 Nov
Foliage Galore! 14mi to Mt. Snow, Arcade, 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 favourite 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 depend 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 AU$394 per night. Entering your travel dates in the search wizard might find you 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?

The Jelly Mill-A Peaceful 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 20 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 Brattleboro Museum & Art Center. Other places in town to visit include Latchis Theatre and Vermont Marketplace.

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.