Brattleboro vacation rentals

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Top-rated vacation rentals in Brattleboro

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

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Guest favorite

Guesthouse 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.

Jun 20 – 27

G$27,350 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 336 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.

Dec 5 – 12

G$23,321 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 427 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.

Jul 6 – 13

G$20,018 GYD per night

Guest favorite

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.

Jan 2 – 9

G$29,300 GYD per night

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 221 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly goats and dogs, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

Nov 22 – 29

G$30,206 GYD per night

Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 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.

Dec 21 – 28

G$19,477 GYD per night

Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 281 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Oct 8 – 15

G$19,001 GYD per night

Guest favorite

Apartment in Brattleboro

4.96 out of 5 average rating, 149 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.

Jul 6 – 13

G$24,752 GYD per night

Guest favorite

Apartment 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.

Sep 12 – 19

G$18,426 GYD per night

Guest favorite

Apartment in Brattleboro

4.96 out of 5 average rating, 281 reviews

Apt in town 2 BR/2 levels in Victorian Farmhouse

We're two blocks from Main Street and it's just a few blocks more to the local theater, art and culture, a variety of excellent restaurants, and walking trails. You’ll love my place because we're so close to town, but not on a main through street, so it's quiet here. My place is good for couples, or a group of friends, solo adventurers, traveling professionals, and for a great get-away.

May 23 – 30

G$31,057 GYD per night

Superhost

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.

May 28 – Jun 4

G$27,498 GYD per night

Guest favorite

Guesthouse 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.

Dec 25 – Jan 1

G$18,800 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Brattleboro vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Brattleboro

Superhost

Bungalow in Brattleboro

4.93 out of 5 average rating, 231 reviews

Healix Luxury Getaway

Jun 8 – 15

G$34,628 GYD per night

Guest favorite

Apartment in Winchester

4.93 out of 5 average rating, 161 reviews

Downtown Loft above Winery and Distillery

Nov 26 – Dec 3

G$17,503 GYD per night

Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 477 reviews

Serenity Now - Couples Retreat or Writer's Dream

Aug 30 – Sep 6

G$38,984 GYD per night

Guest favorite

Cottage in Newfane

4.89 out of 5 average rating, 215 reviews

Ridgeview: Cozy Cottage with a View

Dec 4 – 11

G$29,368 GYD per night

Guest favorite

Apartment in Putney

4.89 out of 5 average rating, 109 reviews

Hip & Cozy Storefront

Nov 2 – 9

G$25,140 GYD per night

Superhost