Vacation rentals in Windham County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windham County

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

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Oct 4 – 11

G$21,834 GYD per night
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.

Nov 25 – Dec 2

G$22,939 GYD 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.

May 5 – 12

G$19,057 GYD per night

Popular amenities for Windham County vacation rentals

Other great vacation rentals in Windham County

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 180 reviews

New Cabin in Jamaica

Sep 16 – 23

G$31,922 GYD per night
Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

Sep 1 – 8

G$24,796 GYD per night
Guest favorite

Tiny home in Dover

4.99 out of 5 average rating, 149 reviews

Rustic Cabin in foothills of Green Mountains

Sep 28 – Oct 5

G$24,197 GYD per night
Guest favorite

Cottage in Newfane

4.99 out of 5 average rating, 171 reviews

Cozy Vermont Antique Sugar House with Fireplace

Mar 3 – 10

G$32,478 GYD per night
Guest favorite

Cabin in Newfane

5.0 out of 5 average rating, 150 reviews

Custom cabin by the river in Newfane, VT

Jun 23 – 30

G$30,025 GYD per night
Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 197 reviews

Light Filled Loft in the Vermont Countryside

Apr 20 – 27

G$24,282 GYD per night
Guest favorite

Home in Newfane

4.95 out of 5 average rating, 169 reviews

Adorable home in Newfane

May 6 – 13

G$28,979 GYD per night
Guest favorite

Apartment in Wilmington

4.88 out of 5 average rating, 278 reviews

Globetrotter Retreat - Minutes to the Mountain

Aug 14 – 21

G$24,050 GYD per night
Superhost

Cabin in Brattleboro

4.89 out of 5 average rating, 441 reviews

Cottage

Aug 14 – 21

G$27,571 GYD per night
Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 260 reviews

A charming VT chalet

May 27 – Jun 3

G$32,571 GYD per night
Guest favorite

Tiny home in Brattleboro

4.95 out of 5 average rating, 173 reviews

"Mountain View" Hike In Cabin Retreat

Aug 24 – 31

G$19,031 GYD per night
Guest favorite

Apartment in Vernon

4.96 out of 5 average rating, 130 reviews

Farm land view.

Apr 20 – 27

G$20,541 GYD per night

Destinations to explore

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