Holiday rentals in Windham

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Top-rated holiday rentals in Windham

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

Guest favourite

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!

4–11 Oct

£96 per night
Guest favourite

Cottage in Londonderry

4.96 out of 5 average rating, 199 reviews

Vermont Treehouse - Romantic Private Elegant

SPECIAL 2 night minimum, self checkin. Work remotely. Enjoy this romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails on property. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

20–27 Oct

£313 per night
Guest favourite

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.

1–8 Nov

£97 per night

Popular amenities for Windham holiday rentals

Stay near Windham's top sights

Magic Mountain Ski Area136 locals recommend
The Upper Pass Lodge3 locals recommend
Hamilton Falls27 locals recommend
The Red Slate Restaurant4 locals recommend
West River Dam3 locals recommend
Tater Hill Golf Course8 locals recommend

Other great holiday rentals in Windham

Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 201 reviews

Log Cabin Near Stratton/Mt Snow

11–18 May

£110 per night
Guest favourite

Cottage in Jamaica

4.82 out of 5 average rating, 461 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

4–11 May

£110 per night
Guest favourite

Home in Putney

4.95 out of 5 average rating, 306 reviews

Cozy Train Depot in Putney Vermont

9–16 Apr

£101 per night
Guest favourite

Apartment in Londonderry

4.95 out of 5 average rating, 42 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

21–28 Jun

£106 per night
Guest favourite

Home in Windham

4.95 out of 5 average rating, 76 reviews

Artistic Southern Vt Countryside Home at Windham

18–25 May

£171 per night
Superhost

Treehouse in Londonderry

4.94 out of 5 average rating, 53 reviews

Romantic Riverbed Treehouse - hot tub & new sauna!

5–12 Mar

£231 per night
Guest favourite

Flat in Londonderry

4.96 out of 5 average rating, 27 reviews

Dog-friendly, 1-bedroom apartment w/ fireplace (A)

13–20 Nov

£149 per night
Guest favourite

Guest house in Grafton

4.89 out of 5 average rating, 90 reviews

VT Sugar House-Guesthouse

20–27 Sept

£67 per night
Guest favourite

Home in Jamaica

5.0 out of 5 average rating, 25 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

15–22 Sept

£154 per night
Guest favourite

Bungalow in Putney

4.96 out of 5 average rating, 27 reviews

Cozy paradise in Westminster West

23–30 Aug

£110 per night
Guest favourite

Loft in Town of Rockingham

5.0 out of 5 average rating, 31 reviews

Saxtons River Studio apartment

30 Nov – 7 Dec

£103 per night
Guest favourite

Apartment in Stratton

4.96 out of 5 average rating, 89 reviews

Premier Stratton Village Location - Pool & Hot Tub

10–17 Apr

£95 per night

Quick stats about holiday rentals in Windham

Total rentals

60 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

1.6K reviews

Nightly prices starting at

£87 before taxes and fees

Destinations to explore

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