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Holiday rentals in Brattleboro

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Top-rated holiday rentals in Brattleboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Bungalow in Brattleboro

4.93 out of 5 average rating, 231 reviews

Healix Luxury Getaway

This charming turn of the century cottage has been mindfully renovated with radiant floor heat and indirect lighting. The space includes vaulted ceilings, large skylight, abundant oxygen providing greenery, and high end bathroom appointments. Previously a yoga studio, it is solely an airbnb now. It's conveniently located off exit 1 on I-91, within walking distance of quaint downtown Brattleboro, with safe and free off-street parking. An entry ramp provides ease of accessibility for all.

8–15 Jun

$225 SGD per night

Guest favourite

Guest house in Brattleboro

4.99 out of 5 average rating, 198 reviews

Light Filled Loft in the Vermont Countryside

Our spacious, tranquil, light-filled Barn Loft is thoughtfully and creatively designed. Complete with a living area, sleeping alcove, flat-screen TV, full kitchen, dining area, and large bathroom with a deluxe shower. A private deck with seating that looks out into our lovely Vermont woods and verdant gardens is attached to the loft. Stay a night or a week, there is plenty to do in every season. We are a friendly, welcoming, worldly, family. We look forward to hosting you at our country home.

20–27 Jun

$179 SGD per night

Guest favourite

Home in Putney

4.94 out of 5 average rating, 335 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

29 Nov – 6 Dec

$151 SGD per night

Guest favourite

Guest house in Brattleboro

4.93 out of 5 average rating, 426 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

3–10 Jul

$140 SGD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

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

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

13–20 Mar

$191 SGD per night

Guest favourite

Guest suite in Brattleboro

4.94 out of 5 average rating, 517 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

9–16 Dec

$127 SGD per night

Guest favourite

Flat in Brattleboro

4.96 out of 5 average rating, 148 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

1–8 May

$162 SGD per night

Guest favourite

Flat in Dummerston

4.96 out of 5 average rating, 158 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

26 Jun – 3 Jul

$120 SGD per night

Guest favourite

Flat in Brattleboro

4.9 out of 5 average rating, 483 reviews

Cozy, Private & Great location for exploring VT !

The apartment is centrally located, cozy, quiet and private. It has been set up to be a comfortable retreat. It's private entrance leads upstairs to an open living room/ kitchen space. The back door opens to a deck overlooking a ball field and green hills. The sleeping nook contains a queen size , metal framed bed. The mattress is comfortable and the sheets are soft. VT charges 10% tax

4–11 Oct

$124 SGD per night

Cabin in Brattleboro

4.89 out of 5 average rating, 441 reviews

Cottage

The "Rustic" cottage is furnished with a queen bed, sofa and dining table. There is a small deck with patio furniture, fire ring with wood supplied, and a gas barbecue. It can accommodate 2 people comfortably. Private with parking. Host in separate house. Wi Fi from Xfinity, but please note that it can be patchy. Roku TV WI FI connected to router.

29 May – 5 Jun

$179 SGD per night

Guest favourite

Guest house in Putney

4.97 out of 5 average rating, 195 reviews

Cozy cottage loft and retreat

Relax and recharge in our peaceful Vermont cottage. Enjoy this sweet getaway with hardwood floors, fast wifi, a fully equipped kitchen, a quiet sleeping loft with a queen size bed, gorgeous natural light, views of surrounding hills and pond, gardens, and your own private entrance and back deck next to the Putney Brook.

13–20 Mar

$123 SGD per night

Guest favourite

Flat in Brattleboro

4.89 out of 5 average rating, 314 reviews

Quiet St in Town, gardens, terrace

Private entry, up wide covered stairs to open and enclosed porches, into newly renovated spacious open concept living and kitchen area. Separate large BR with queen-size bed has French doors that open onto the enclosed porch. A few blocks to downtown restaurants, food coop, and shops, walking distance to trails.

27 Apr – 4 May

$163 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Brattleboro holiday rentals

Free parking on premises

Air conditioning

Stay near Brattleboro's top sights

Brattleboro Food Co-Op102 locals recommend

The Marina59 locals recommend

Whetstone Station Restaurant and Brewery116 locals recommend

The Vermont Country Deli29 locals recommend

99 Restaurants7 locals recommend

Price Chopper11 locals recommend

Other great holiday rentals in Brattleboro

Guest favourite

Flat in Marlboro

4.94 out of 5 average rating, 221 reviews

Shakespeare’s Folly Side Farm and AirBnB.

19–26 Mar

$197 SGD per night

Guest favourite

Flat in Winchester

4.93 out of 5 average rating, 160 reviews

Downtown Loft above Winery and Distillery

1–8 Nov

$110 SGD per night

Guest favourite

Flat in Putney

4.89 out of 5 average rating, 109 reviews

Hip & Cozy Storefront

14–21 Dec

$160 SGD per night

Guest favourite

Guest house in Putney

4.93 out of 5 average rating, 244 reviews

Relax At the End of the Road

9–16 Sep

$170 SGD per night

Guest favourite

Home in Guilford

4.94 out of 5 average rating, 173 reviews

Peaceful Country Home

30 Mar – 6 Apr

$208 SGD per night

Guest favourite

Tiny home in Brattleboro

4.94 out of 5 average rating, 34 reviews

Sweet Vermont Tiny Home Get Away

27 Dec – 3 Jan

$115 SGD per night

Guest favourite

Flat in Brattleboro

4.99 out of 5 average rating, 73 reviews

River View apartment 30 minutes to Mt Snow.

5–12 Mar

$191 SGD per night

Guest favourite

Tiny home in Brattleboro

5.0 out of 5 average rating, 8 reviews

Brattleboro Tiny House

14–21 May

$185 SGD per night

Quick stats about holiday rentals in Brattleboro

Total rentals	90 properties
Rentals with dedicated workspaces	40 properties have a dedicated workspace
Pet-friendly rentals	20 properties allow pets
Family-friendly rentals	30 properties are a good fit for families
Total number of reviews	6.4K reviews
Nightly prices starting at	$41 SGD before taxes and fees

Destinations to explore