Brattleboro vacation rentals

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Top-rated vacation rentals in Brattleboro

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Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 199 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.

Jul 17 – 24

G$27,460 GYD per night

Guest favorite

Home in Putney

4.94 out of 5 average rating, 337 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.

Oct 23 – 30

G$21,066 GYD per night

Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 429 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.

Jun 30 – Jul 7

G$22,242 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.

Aug 26 – Sep 2

G$29,244 GYD per night

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 223 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.

Mar 18 – 25

G$30,113 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 24 – 31

G$19,439 GYD per night

Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 283 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 .

Jul 23 – 30

G$18,964 GYD per night

Guest favorite

Apartment in Brattleboro

4.95 out of 5 average rating, 150 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.

May 10 – 17

G$24,704 GYD per night

Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 479 reviews

Serenity Now - Couples Retreat or Writer's Dream

COUPLES RETREAT or SOLO EXCURSION Perfect setting to swoon your partner or write the novel of your dreams. A romantic destination for Engagements, Honeymoons & Anniversaries. Guilford Vermont - no cleaning fee - Easy drive from Boston & NYC ROMANCE SPECIAL - Guests staying 3 nights or more, receive hard cider, cheese and chocolate ($50.00 value) Ask me about ELOPEMENT & VOW RENEWAL CEREMONIES

Mar 16 – 23

G$37,939 GYD per night

Guest favorite

Apartment in Brattleboro

4.96 out of 5 average rating, 284 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 1 – 8

G$28,714 GYD per night

Guest favorite

Apartment in Dummerston

4.93 out of 5 average rating, 366 reviews

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn 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.

Oct 2 – 9

G$21,583 GYD per night

Superhost

Cabin in Brattleboro

4.89 out of 5 average rating, 442 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.

Sep 27 – Oct 4

G$27,444 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

Tiny home in Brattleboro

4.86 out of 5 average rating, 166 reviews

“Sugar Maple” Rustic Cabin Getaway with Fireplace

Jan 5 – 12

G$19,942 GYD per night

Guest favorite

Bungalow in Brattleboro

4.93 out of 5 average rating, 232 reviews

Healix Luxury Getaway

Jun 13 – 20

G$34,416 GYD per night

Guest favorite

Cabin in Brattleboro

4.95 out of 5 average rating, 130 reviews

Peaceful rural cabin on beautiful large property

May 11 – 18

G$33,463 GYD per night

Guest favorite

Cottage in Newfane

4.89 out of 5 average rating, 216 reviews

Ridgeview: Cozy Cottage with a View

Dec 6 – 13

G$29,310 GYD per night

Guest favorite

Apartment in Winchester

4.93 out of 5 average rating, 162 reviews

Downtown Loft above Winery and Distillery

Aug 27 – Sep 3

G$20,187 GYD per night

Guest favorite

Apartment in Putney

4.89 out of 5 average rating, 110 reviews

Hip & Cozy Storefront

Jan 12 – 19

G$24,534 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

Sep 4 – 11

G$21,418 GYD per night

Guest favorite

Home in Guilford

4.94 out of 5 average rating, 173 reviews

Peaceful Country Home

Mar 24 – 31

G$31,817 GYD per night

Show all

Other great vacation rentals in Brattleboro

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 140 reviews

Beautiful Timber Frame Retreat

Sep 30 – Oct 7

G$46,009 GYD per night

Guest favorite

Apartment in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

Jan 9 – 16

G$32,224 GYD per night

Guest favorite

Cabin in Newfane

4.99 out of 5 average rating, 238 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Nov 14 – 21

G$54,012 GYD per night

Superhost

Home in Putney

4.84 out of 5 average rating, 121 reviews

Spacious Loft with View

Dec 17 – 24

G$35,150 GYD per night

Guest favorite

Apartment in Putney

4.92 out of 5 average rating, 114 reviews

Private West Hill Apartment

Nov 23 – 30

G$24,869 GYD per night

Guest favorite

Cabin in Putney

4.98 out of 5 average rating, 355 reviews

Vermont Retreat Cottage| Paradise in Nature

Nov 11 – 18

G$45,999 GYD per night

Guest favorite

Tiny home in Brattleboro

4.94 out of 5 average rating, 36 reviews

Sweet Vermont Tiny Home Get Away

Jul 17 – 24

G$20,489 GYD per night

Guest favorite

Apartment in Brattleboro

4.94 out of 5 average rating, 16 reviews

Bright and Modern Chestnut Street Apartment

Jul 8 – 15

G$26,786 GYD per night

Show all

Quick stats about vacation 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
G$6,255 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Brattleboro?
Yes! Work meets play with ease at over 40 vacation rentals in Brattleboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Brattleboro?
Four-legged friends are welcome in Brattleboro. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly apartment rentals in Brattleboro?
Brattleboro has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Brattleboro have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Brattleboro. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Brattleboro have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Brattleboro. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Brattleboro?
Experience the best of Brattleboro with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Brattleboro have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Brattleboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Brattleboro?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Brattleboro vacation rentals

Top-rated vacation rentals in Brattleboro

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Brattleboro vacation rentals

Stay near Brattleboro's top sights

Other great vacation rentals in Brattleboro

Tiny home in Brattleboro

Bungalow in Brattleboro

Cabin in Brattleboro

Cottage in Newfane

Apartment in Winchester

Apartment in Putney

Barn in Chester

Home in Guilford

Other great vacation rentals in Brattleboro

Tiny home in Wilmington

Apartment in Newfane

Cabin in Newfane

Home in Putney

Apartment in Putney

Cabin in Putney

Tiny home in Brattleboro

Apartment in Brattleboro

Quick stats about vacation rentals in Brattleboro

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Brattleboro?

Are there pet-friendly vacation rentals in Brattleboro?

Are there family-friendly apartment rentals in Brattleboro?

Do house rentals in Brattleboro have air conditioning?

Do house rentals in Brattleboro have a bbq area?

How much does it cost to stay in apartment rentals in Brattleboro?

Do apartment rentals in Brattleboro have wifi?

What are the most popular amenities for House Rentals in Brattleboro?

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