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House vacation rentals in Windham County

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Top-rated house rentals in Windham County

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Home in Putney

4.84 out of 5 average rating, 121 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Nov 19 – 26

G$35,179 GYD per night

Home in Jamaica

5.0 out of 5 average rating, 100 reviews

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

May 28 – Jun 4

G$90,617 GYD per night

Home in Putney

4.94 out of 5 average rating, 338 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.

Apr 12 – 19

G$23,091 GYD per night

Home in Wilmington

4.99 out of 5 average rating, 171 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

May 27 – Jun 3

G$44,784 GYD per night

Home in Winhall

4.98 out of 5 average rating, 135 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Jul 16 – 23

G$85,668 GYD per night

Home in West Brattleboro

4.86 out of 5 average rating, 125 reviews

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Mar 24 – 31

G$37,798 GYD per night

Home in Newfane

4.97 out of 5 average rating, 114 reviews

Peaceful cabin close to skiing & Brattleboro

Our 4BR/2BA (+ outdoor summer shower) home embraces the best of Southern VT. Skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants nearby. Open concept space, cook's kitchen, jet bathtub, beautiful gardens, winter hot tub off deck, and large patio and fireplace give a homey feel. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat for your next gathering.

Jan 9 – 16

G$64,492 GYD per night

Home in Dover

4.87 out of 5 average rating, 227 reviews

Mt Snow retreat, ski & summer

COVID-19: We block two days between all bookings and have committed to the Airbnb cleaning policy. Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up.

Oct 2 – 9

G$32,817 GYD per night

Home in Townshend

4.94 out of 5 average rating, 193 reviews

Comfy and Cozy House on 67 acres

67 acre of wilderness to explore, a calm and relaxed getaway. Bright, spacious main room and open kitchen with wood stove is enclosed by the large porch which looks over the Vermont woodlands. Right off of the large entryway, you'll find the sweeping main bedroom equipped with an open soaking tub, and a second wood stove, along with a separate entrance. Finally, there is a separate bedroom downstairs with its own bathroom (off of garage).

Feb 3 – 10

G$44,620 GYD per night

Home in Winhall

4.99 out of 5 average rating, 349 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Sep 14 – 21

G$64,708 GYD per night

Home in Dummerston

4.99 out of 5 average rating, 323 reviews

Pinecone Pond

Spring skiing still happening just a short ride away! As of March 23, fresh snow at Mt Snow and Stratton!Nestled in the heart of southern Vermont, Pinecone Pond is a truly special getaway that offers great views, large pond, babbling brook, privacy, and a short ride to Mt Snow, Stratton, Putney, or Brattleboro!

Feb 7 – 14

G$81,590 GYD per night

Home in Newfane

4.95 out of 5 average rating, 170 reviews

Adorable home in Newfane

3 bedroom, 1 bath home. Fully equipped kitchen, cable and internet access. Pastoral meadow view. Quiet road. Private back yard with patio. Bordering on town forest. Close to popular swimming holes. 25 minutes to Mt. Snow, 15-18 to Brattleboro and Putney

Oct 22 – 29

G$28,870 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windham County house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Wilmington

4.9 out of 5 average rating, 130 reviews

4 bedroom Ski House 15 min to Mount Snow

May 15 – 22

G$34,489 GYD per night

Home in Wilmington

4.88 out of 5 average rating, 150 reviews

Adams Farm-"The Little Farmhouse"

Aug 20 – 27

G$53,612 GYD per night

Home in Wilmington

4.83 out of 5 average rating, 155 reviews

The Vermont Barn (Mount Snow)

Apr 6 – 13

G$66,575 GYD per night

Home in Peru

4.92 out of 5 average rating, 139 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Nov 18 – 25

G$72,320 GYD per night

Home in Wardsboro

5.0 out of 5 average rating, 11 reviews

Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton

Nov 22 – 29

G$69,493 GYD per night

Home in Wardsboro

5.0 out of 5 average rating, 30 reviews

Mt Snow/Stratton Getaway w/Hot Tub, Fire Pit + AC!

Aug 26 – Sep 2

G$127,610 GYD per night

Home in Wilmington

4.9 out of 5 average rating, 20 reviews

Mountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow

Nov 11 – 18

G$82,583 GYD per night

Home in Wilmington

4.77 out of 5 average rating, 13 reviews

Chimney Hill Retreat w/ Amenity Center & Fireplace

Jun 15 – 22

G$36,470 GYD per night

Weekly house rentals

Home in Wilmington

4.94 out of 5 average rating, 241 reviews

Wilmington. Easy walk to center of town.

Oct 6 – 13

G$50,380 GYD per night

Home in South Londonderry

4.86 out of 5 average rating, 99 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Mar 5 – 12

G$84,052 GYD per night

Home in Grafton

4.92 out of 5 average rating, 186 reviews

Retro Modern Barn Apartment

Oct 31 – Nov 7

G$41,922 GYD per night

Home in Putney

4.85 out of 5 average rating, 233 reviews

Preston’s Pond-Beautiful home on Tranquil Hilltop

Apr 16 – 23

G$36,815 GYD per night

Home in Town of Rockingham

4.89 out of 5 average rating, 113 reviews

Beautiful Home in the Mountains - The Fox & Owl

Jun 16 – 23

G$41,908 GYD per night

Home in Jamaica

4.96 out of 5 average rating, 158 reviews

Cozy Riverfront Home in beautiful Jamaica

Dec 13 – 20

G$59,298 GYD per night

Home in Jamaica

4.84 out of 5 average rating, 232 reviews

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Oct 9 – 16

G$38,134 GYD per night

Home in Weston

4.95 out of 5 average rating, 227 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Aug 23 – 30

G$52,328 GYD per night

Private house rentals

Home in Townshend

4.96 out of 5 average rating, 73 reviews

Cozy, Comfy Country Home in Southern VT Village

Oct 16 – 23

G$32,352 GYD per night

Home in Guilford

4.9 out of 5 average rating, 30 reviews

Woodland Retreat in Maple Sugarbush, EV

May 13 – 20

G$28,741 GYD per night

Home in Chesterfield

4.92 out of 5 average rating, 86 reviews

Governer's Brook Camp - 2 Bedroom

Jul 4 – 11

G$26,424 GYD per night

Home in Jamaica

4.89 out of 5 average rating, 64 reviews

The Post Haus: one-of-a-kind modern VT experience

Sep 12 – 19

G$79,355 GYD per night

Home in Chesterfield

4.95 out of 5 average rating, 41 reviews

The River House

Sep 19 – 26

G$37,204 GYD per night

Home in Whitingham

4.97 out of 5 average rating, 61 reviews

Gorgeous farmhouse beautiful view pond/mountains

May 6 – 13

G$34,029 GYD per night

Home in West Brattleboro

4.95 out of 5 average rating, 66 reviews

Private Brookside Farmhouse

Apr 16 – 23

G$36,215 GYD per night

Home in West Brattleboro

4.91 out of 5 average rating, 93 reviews

Modern Spacious Home with Mountain Views

Dec 5 – 12

G$42,973 GYD per night

Destinations to explore