Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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

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.

Oct 19 – 26

G$70,546 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

Popular amenities for Windham vacation 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 vacation rentals in Windham

Guest favorite

Cottage in Jamaica

4.82 out of 5 average rating, 461 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

May 8 – 15

G$23,019 GYD per night
Superhost

Cottage in Chester

4.91 out of 5 average rating, 151 reviews

Green Mountain Country Cottage

Nov 11 – 18

G$55,223 GYD per night
Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 42 reviews

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

Jun 21 – 28

G$21,971 GYD per night
Guest favorite

Apartment in Londonderry

4.95 out of 5 average rating, 22 reviews

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

Sep 22 – 29

G$28,697 GYD per night
Guest favorite

Home in Windham

4.95 out of 5 average rating, 76 reviews

Artistic Southern Vt Countryside Home at Windham

May 18 – 25

G$37,589 GYD per night
Superhost

Treehouse in Londonderry

4.94 out of 5 average rating, 53 reviews

Romantic Riverbed Treehouse - hot tub & new sauna!

Feb 25 – Mar 4

G$51,436 GYD per night
Guest favorite

Guesthouse in Grafton

4.89 out of 5 average rating, 90 reviews

VT Sugar House-Guesthouse

Oct 22 – 29

G$15,151 GYD per night
Guest favorite

Home in Jamaica

5.0 out of 5 average rating, 25 reviews

2-Bedroom Home, 7 Minutes From Stratton Mountain

Sep 30 – Oct 7

G$32,807 GYD per night
Guest favorite

Bungalow in Putney

4.96 out of 5 average rating, 27 reviews

Cozy paradise in Westminster West

Aug 22 – 29

G$25,069 GYD per night
Guest favorite

Loft in Town of Rockingham

5.0 out of 5 average rating, 31 reviews

Saxtons River Studio apartment

Nov 29 – Dec 6

G$24,007 GYD per night
Guest favorite

Loft in Jamaica

4.98 out of 5 average rating, 93 reviews

Cozy Loft for your Southern VT Adventures

Jun 9 – 16

G$18,454 GYD per night
Guest favorite

Cabin in Londonderry

4.96 out of 5 average rating, 95 reviews

Summit view cottage: Secluded cabin with hot tub

Oct 30 – Nov 6

G$84,712 GYD per night

Quick stats about vacation 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

G$23,039 GYD before taxes and fees

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Windham have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Windham?

    Experience the best of Windham with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Windham have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Windham?

    Windham has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Windham?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Windham have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Windham?

    Yes! Work meets play with ease at over 30 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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