Windham, VT

Travel Guide

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT
Book a stay at this ski vacation home in West Townshend. Enjoy free WiFi, private pools, and a sauna. Popular attractions Magic Mountain Ski Resort and Lowell ...
10/10 Exceptional! (67 reviews)
"We loved this property - had great amenities, location, & check in process very smooth. The host was very communicative. Would definitely recommend to others!"

Reviewed on Sep 27, 2026

Get rates
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
$172 nightly
The price is $189 total per night from Nov 10 to Nov 11
$189 total
Nov 10 - Nov 11
Total with taxes and fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
8.6/10 Excellent! (330 reviews)
"The room and atmosphere of the hotel was amazing. But we came on the off season and a lot of things were closed. The restaurant and spa were closed but also a bunch of the restaurants in the area were closed on a Saturday night for dinner. But again this was an off season so I get it."

Reviewed on Nov 8, 2026

Grand Summit Resort, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
$204 nightly
The price is $224 total per night from Nov 18 to Nov 19
$224 total
Nov 18 - Nov 19
Total with taxes and fees
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
Jackson Gore Village, A Vail Resorts Property
See all 2,609 properties in Windham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT
Book a stay at this ski vacation home in West Townshend. Enjoy free WiFi, private pools, and a sauna. Popular attractions Magic Mountain Ski Resort and Lowell ...
10/10 Exceptional! (67 reviews)
"We loved this property - had great amenities, location, & check in process very smooth. The host was very communicative. Would definitely recommend to others!"

Reviewed on Sep 27, 2026

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton

Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton

Windham VT
Stay at this chalet in West Townshend. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Magic Mountain Ski Resort and Lowell Lake State Park ...
10/10 Exceptional! (6 reviews)
"Chalet was cozy and perfect for an October weekend getaway with my husband and our Labrador retriever. We loved having coffee on the deck in the morning. Was very peaceful and quiet. Bathrooms and kitchen updated and clean. Michelle and Dave are great hosts and gave thorough check-in instructions ..."

Reviewed on Oct 25, 2026

Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.6/10 Excellent! (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."

Reviewed on Oct 11, 2026

Long Trail House at Stratton Mountain Resort
See all properties in Windham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

When is the best time to visit Windham?
The best time to visit Windham is from July through September, when the destination is most popular. For travelers seeking fewer crowds and potentially better value, the quieter months of October through December are a good choice. This period offers cooler weather and the start of the snowy season.
What cuisines can you find in Windham?
In Windham you can find Mediterranean cuisine, with dishes like hummus, falafel, and gyros. Travelers can also enjoy Italian, North American, and Mexican food, along with various Asian options. The area also offers coffee shops and speakeasy-style bars.
Can I book a refundable hotel in Windham?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Windham by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Windham with Expedia?
Expedia makes it easier to plan your Windham trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Windham?
The best choice depends on your travel style. Hotels in Windham can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Windham trip on Expedia?
Once you've booked your Windham trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Windham trip?
Expedia offers customer support before, during, and after your Windham trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Windham?
If it's your first trip to Windham, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Windham hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Windham hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Windham

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Chester

A snow-covered landscape with a bench and trees.

Londonderry

A snow-covered landscape with a wooden shelter and a clear blue sky.

Grafton

A road flanked by dense bamboo groves.

Jamaica

Explore a world of travel with Expedia