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.

Guest favorite

Home in Putney

4.94 out of 5 average rating, 332 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.

Aug 30 – Sep 6

R1,802 ZAR per night
Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 197 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 16 – 23

R2,485 ZAR per night
Guest favorite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 421 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 12 – 19

R1,881 ZAR per night

Popular amenities for Brattleboro vacation rentals

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

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 220 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Sep 5 – 12

R2,770 ZAR per night
Superhost

Bungalow in Brattleboro

4.93 out of 5 average rating, 229 reviews

Healix Luxury Getaway

Apr 11 – 18

R3,128 ZAR per night
Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 476 reviews

Serenity Now - Couples Retreat or Writer's Dream

Dec 28 – Jan 4

R3,451 ZAR per night
Guest favorite

Barn in Chester

4.99 out of 5 average rating, 487 reviews

Inviting studio apartment above barn in Vermont

Apr 22 – 29

R1,704 ZAR per night
Guest favorite

Apartment in Putney

4.89 out of 5 average rating, 107 reviews

Hip & Cozy Storefront

Nov 9 – 16

R2,231 ZAR per night
Guest favorite

Apartment in Marlboro

4.95 out of 5 average rating, 112 reviews

Southern Vermont Sweet Spot

Aug 25 – Sep 1

R1,939 ZAR per night
Guest favorite

Guesthouse in Putney

4.93 out of 5 average rating, 244 reviews

Relax At the End of the Road

Nov 9 – 16

R2,361 ZAR per night
Guest favorite

Tiny home in Jamaica

4.94 out of 5 average rating, 1136 reviews

Apple Blossom Cottage: A Tiny House

Oct 15 – 22

R1,855 ZAR per night
Guest favorite

Cottage in Newfane

4.89 out of 5 average rating, 212 reviews

Ridgeview: Cozy Cottage with a View

Oct 21 – 28

R2,666 ZAR per night
Superhost

Cottage in Putney

4.81 out of 5 average rating, 226 reviews

The Cottage, a house built for guests.

Mar 16 – 21

R1,709 ZAR per night
Guest favorite

Cabin in Brattleboro

4.95 out of 5 average rating, 129 reviews

Peaceful rural cabin on beautiful large property

Apr 3 – 10

R3,044 ZAR per night
Superhost

Home in Putney

4.84 out of 5 average rating, 118 reviews

Spacious Loft with View

May 17 – 24

R3,197 ZAR per night

Other great vacation rentals in Brattleboro

Guest favorite

Home in West Brattleboro

4.86 out of 5 average rating, 123 reviews

Cozy Home for 2-5 People in Vermont

Dec 4 – 11

R3,435 ZAR per night
Guest favorite

Home in Guilford

4.94 out of 5 average rating, 173 reviews

Peaceful Country Home

Mar 10 – 17

R2,894 ZAR per night
Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 258 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apr 30 – May 7

R1,988 ZAR per night
Guest favorite

Cabin in Newfane

4.99 out of 5 average rating, 234 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

Dec 2 – 9

R4,912 ZAR per night
Guest favorite

Home in Newfane

4.95 out of 5 average rating, 169 reviews

Adorable home in Newfane

Oct 24 – 31

R2,623 ZAR per night
Guest favorite

Tiny home in Orange

4.92 out of 5 average rating, 310 reviews

The Writer's Retreat: A Sweetwater Stay

Nov 13 – 20

R2,238 ZAR per night
Guest favorite

Cabin in Newfane

5.0 out of 5 average rating, 150 reviews

Custom cabin by the river in Newfane, VT

Mar 1 – 8

R2,718 ZAR per night
Guest favorite

Apartment in Brattleboro

4.99 out of 5 average rating, 71 reviews

River View apartment 30 minutes to Mt Snow.

May 26 – Jun 2

R2,551 ZAR per night
Superhost

Cabin in Brattleboro

4.93 out of 5 average rating, 46 reviews

Solar Cabin Farmstay

May 22 – 29

R2,194 ZAR per night
Guest favorite

Home in West Brattleboro

4.91 out of 5 average rating, 32 reviews

Beautiful nature retreat minutes to Brattleboro

May 12 – 19

R2,510 ZAR per night
Guest favorite

Tiny home in Brattleboro

5.0 out of 5 average rating, 6 reviews

Brattleboro Tiny House

May 17 – 24

R2,320 ZAR per night
Guest favorite

Treehouse in Guilford

4.99 out of 5 average rating, 82 reviews

Cozy tent in the trees on organic flower farm

Jan 6 – 13

R2,402 ZAR per night

Quick stats about vacation rentals in Brattleboro

Total rentals

80 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

6.1K reviews

Nightly prices starting at

R569 ZAR 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 apartment rentals in Brattleboro have air conditioning?

    Absolutely! We offer over 20 apartment 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 20 homes with wifi, over 10 homes with a bbq area, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Brattleboro