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Holiday homes in Windham You’ll Love

Top-Rated Windham Holiday homes for Every Budget and Style!

Looking for a holiday home in Windham (Vermont)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Windham.

We found 17 Holiday-homes in Windham and the surrounding area (within 30 miles)

Green Mountain Getaway in Jamaica, USA

Green Mountain Getaway

Holiday home in Jamaica near Windham, Vermont
Green Mountain Getaway is located in Jamaica, just 18 miles from Mount Equinox and 20 miles from Emerald Lake State Park.
  • Parking
  • Pets allowed

no reviews

from $212.67 Show details »

Sweet Berry Farm in Jamaica, USA

Sweet Berry Farm

Holiday home in Jamaica near Windham, Vermont
Sweet Berry Farm is located in Jamaica, just 17 miles from Mount Equinox and 19 miles from Emerald Lake State Park.
  • Parking

No reviews yet 1 Reviews 1.0

from $1.437.66 Show details »

Beautiful chalet near Stratton in Jamaica, USA

Beautiful chalet near Stratton

Holiday home in Jamaica near Windham, Vermont , 72 Landman Lane
Offering a garden, Beautiful chalet near Stratton provides accommodations in Jamaica.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $81.00 Show details »

Turner Hill Cottage in West Townshend, USA

Turner Hill Cottage

Holiday home in West Townshend near Windham, Vermont
Turner Hill Cottage is located in West Townshend, just 30 miles from Mount Equinox and 14 miles from Bellows Falls Amtrak Station.
  • Parking

no reviews

from $174.33 Show details »

Green Mountain base camp for year-round adventure! in Londonderry, USA

Green Mountain base camp for year-round...

Holiday home in Londonderry near Windham, Vermont , 643 Deerwood Hill
Offering a garden, Green Mountain base camp for year-round adventure! features accommodations in Londonderry.
  • Parking

Exceptional 2 Reviews 10.0

from $306.60 Show details »

Beauchamp Hill in Londonderry, USA

Beauchamp Hill

Holiday home in Londonderry near Windham, Vermont
Beauchamp Hill is located in Londonderry, just 16 miles from Mount Equinox and 18 miles from Emerald Lake State Park.
  • Parking

no reviews

from $463.67 Show details »

Cozy Cabin in the Woods in Londonderry, USA

Cozy Cabin in the Woods

Holiday home in Londonderry near Windham, Vermont
Cozy Cabin in the Woods offers accommodations in Londonderry, 18 miles from Mount Equinox and 20 miles from Emerald Lake State Park.
  • Parking

no reviews

from $238.98 Show details »

Magic Birch Lodge in Windham, USA

Magic Birch Lodge

Holiday home in Windham, Vermont
Magic Birch Lodge is located in Windham, just 21 miles from Mount Equinox and 22 miles from Dorsey Park.
  • Parking

Superb 13 Reviews 9.2

from $150.09 Show details »

The Greens at Londonderry Links in Londonderry, USA

The Greens at Londonderry Links

Holiday home in Londonderry near Windham, Vermont , 482 Middletown Rd, Londonderry, VT 05155, USA
The Greens at Londonderry Links offers accommodations in Londonderry, 18 miles from Mount Equinox and 19 miles from Emerald Lake State Park.

no reviews

from $485.33 Show details »

Vermont Ski Chalet about 5 Mi to Magic Mountain in Windham, USA

Vermont Ski Chalet about 5 Mi to Magic M...

Holiday home in Windham, Vermont
Vermont Ski Chalet about 5 Mi to Magic Mountain offers accommodations in Windham, 17 miles from Stratton Mountain and 21 miles from Mount Equinox.
  • Parking

no reviews

from $403.57 Show details »

half Mi to Ski Secluded Home in Vermont in Londonderry, USA

half Mi to Ski Secluded Home in Vermont

Holiday home in Londonderry near Windham, Vermont
Half Mi to Ski Secluded Home in Vermont offers accommodations in Londonderry, 14 miles from Stratton Mountain and 18 miles from Mount Equinox.
  • Parking

no reviews

from $331.09 Show details »

South Londonderry Home, Walk to Magic Mtn Ski Area in Londonderry, USA

South Londonderry Home, Walk to Magic Mt...

Holiday home in Londonderry near Windham, Vermont
South Londonderry Home, Walk to Magic Mtn Ski Area is located in Londonderry, just 25 miles from Bellows Falls Amtrak Station and 26 miles from Skylin...
  • Parking
  • Spa and wellness centre

no reviews

from $398.24 Show details »

Award-Winning Log Cabin, Top 5 in New England! in Londonderry, USA

Award-Winning Log Cabin, Top 5 in New En...

Holiday home in Londonderry near Windham, Vermont
Award-Winning Log Cabin, Top 5 in New England! offers accommodations in Londonderry, 15 miles from Mount Equinox and 16 miles from Dorsey Park.
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $313.60 Show details »

Londonderry Chalet with Deck, Fire Pit and Views! in Londonderry, USA

Londonderry Chalet with Deck, Fire Pit a...

Holiday home in Londonderry near Windham, Vermont
Londonderry Chalet with Deck, Fire Pit and Views! offers accommodations in Londonderry, 20 miles from Mount Equinox and 21 miles from Dorsey Park.
  • Parking

Exceptional 1 Reviews 10.0

from $356.00 Show details »

Londonderry Retreat about 3 Mi to Lowell Lake! in Londonderry, USA

Londonderry Retreat about 3 Mi to Lowell...

Holiday home in Londonderry near Windham, Vermont
Londonderry Retreat about 3 Mi to Lowell Lake! is located in Londonderry, just 15 miles from Mount Equinox and 15 miles from Dorsey Park.
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $322.72 Show details »

The Loft at Pine Rock in Weston, USA

The Loft at Pine Rock

Holiday home in Weston near Windham, Vermont
The Loft at Pine Rock is located in Weston, just 18 miles from Mount Equinox and 13 miles from Dorsey Park.
  • Parking
  • Pets allowed

no reviews

from $195.32 Show details »

Contemporary Magic Mountain Chalet Close to Skiing, Hiking, Fun in Londonderry, USA

Contemporary Magic Mountain Chalet Close...

Chalet in Londonderry near Windham, Vermont , 199 Magic Circle
A recently renovated chalet, Contemporary Magic Mountain Chalet Close to Skiing, Hiking, Fun offers accommodations in Londonderry.
  • Parking
  • Family rooms

Very good 2 Reviews 8.5

from $262.84 Show details »

Number of Holiday homes in Windham 17
Number of guest ratings 13
Average price per night $332.00
Lowest price per night $50,00
Highest price per night $2.192,62

Top 10 Cheapest Holiday-homes in Windham

Discover the Cheapest Holiday-homes in Windham – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Windham

Check out the Most Booked Holiday-homes in Windham – Based on Guest Popularity.

Holiday homes in Windham (Vermont), comfortable and familiar

Staying in a holiday or vacation home in Windham can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Windham for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Windham should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com