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Find Extended Stay Hotels in Windsor, VT

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Top Windsor Extended Stay Hotels | Reserve now, pay later

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

3.0 star property
9.2 out of 10, Wonderful, (359)
"good rooms an good staff!"
$167 nightly
The price is $181
Oct 28 - Oct 29
Total with taxes and fees
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1019)
"We have stayed here a few times and continue to enjoy our stay every time. We will keep staying here when in the area. "
$130 nightly
The price is $143
Oct 15 - Oct 16
Total with taxes and fees
North Star Lodge and Resort

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (892)
"One day stay all went well"
$137 nightly
The price is $149
Oct 20 - Oct 21
Total with taxes and fees
Pointe at Castle Hill Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (755)
"It is Good place to stay. We enjoyed our stay here."
$197 nightly
The price is $214
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

White River Inn and Suites

2.5 star property
7.0 out of 10, Good, (1019)
"Great place "
$129 nightly
The price is $142
Oct 19 - Oct 20
Total with taxes and fees
White River Inn and Suites

Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

9.8 out of 10, Exceptional, (6)
"Was a great location close to the mountain, comfortable and clean, an excellent stay. Walls were a bit thin, but others on property were respectful and quiet. Really enjoyed our stay for a weekend!"
$188 nightly
The price is $204
Sep 30 - Oct 1
Total with taxes and fees
Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (131)
"Such a great, comfortable place to stay with an awesome staff!"
$189 nightly
The price is $208
Sep 30 - Oct 1
Total with taxes and fees
The Trailside Inn

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
$286 nightly
The price is $311
Oct 29 - Oct 30
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Après Inn Killington

2.0 star property
9.4 out of 10, Exceptional, (145)
"Nice clean rooms very convenient for our road trip through the Adirondacks "
$132 nightly
The price is $145
Oct 28 - Oct 29
Total with taxes and fees
Après Inn Killington

Brook Road Cabin

3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
$321 nightly
The price is $348
Sep 30 - Oct 1
Total with taxes and fees
Brook Road Cabin
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.

Find out more about Windsor

Find out more about Windsor

Discover top Windsor attractions

Windsor, Vermont, is a hidden gem that offers a delightful mix of history, nature, and family-friendly activities perfect for the Quality Seeker. Start your visit at the picturesque Old Windsor Village, where you can stroll through charming streets lined with historic buildings and enjoy local shops that showcase artisan crafts. Don’t miss the American Precision Museum, where you can engage with interactive exhibits that highlight the region's industrial heritage—an exciting educational experience for both kids and adults. For outdoor enthusiasts, the nearby Mount Ascutney State Park offers stunning hiking trails and breathtaking views, providing a perfect backdrop for family adventures. If you’re looking for a unique way to unwind, consider booking a guided kayak tour on the Connecticut River, where you can immerse yourself in the tranquil beauty of Vermont's landscapes. After a day of exploration, the area surrounding the village features several top hotels, such as The Windsor Mansion Inn, which combines comfort with personalized service, ensuring your family's stay is both enjoyable and relaxing. With attentive staff ready to cater to your needs, you’ll feel pampered while enjoying the vibrant local culture.

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Most booked related extended stays in Windsor in 2025

Frequently asked questions

Why book an extended stay hotel in Windsor through Expedia?
From our special offers to our rewards programs, you'll save big when you reserve your extended stay in Windsor through Expedia. Enter your travel dates to discover our selection of long-term rentals, then narrow the results using our filter tool to find your ideal retreat. Our extended stay hotels in Windsor come with amenities like kitchens, laundries and recreational facilities to help make your long-term stay feel homey. Whether you're looking for a hotel for a quick stay or a property with budget-friendly weekly rates, Expedia can help you find the right place.
What can I expect from an extended stay hotel?
With amenities such as kitchens, laundries and dining spaces, extended stay hotels in Windsor can be a convenient and economical alternative to your standard accommodations. Whip up your own tasty meals and save on laundromat bills. Sometimes offering discounted weekly rates, extended stay hotels range from studios for one to spacious and luxurious options with a few rooms. They also offer many of the amenities you'd find in a standard hotel, like housekeeping or 24/7 guest services. If you need flexibility, privacy and a comfortable retreat for a few weeks or more, an extended stay hotel is a wonderful choice.

Top Windsor Hotel Reviews

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Explore a world of travel with Expedia