Hotels in Windsor

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Dates

December 2025

January 2026

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Where to stay in Windsor?

$134 nightly

Dec 18 - Dec 19

Total with taxes and fees

$204 nightly

Dec 14 - Dec 15

Total with taxes and fees

$127 nightly

Dec 21 - Dec 22

Total with taxes and fees

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Go beyond your typical stay in Windsor

Pet friendly

Pool

Top landmarks in Windsor

Brownsville Trail

Travelers who enjoy the great outdoors might want to go to Brownsville Trail, located 3.1 mi (4.9 km) from central Windsor.

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La rivière Otter Creek pour aller à Vergennes, Vermont.

Paradise Park

Paradise Park is 0.7 mi (1.1 km) from central Windsor, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? Want to stretch your legs some more? Head to Cornish State Wildlife Management Area and Path of Life Garden, both nearby.

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American Precision Museum

American Precision Museum is 0.4 mi (0.6 km) from central Windsor, why not stop by during your stay. Why not take a stroll along the riverfront and watch the sunset while you're here? If you want to experience more of the culture Windsor has to offer, head to Cornish-Windsor Covered Bridge, Blow-Me-Down Bridge, and Mt Ascutney Hospital and Health Center: Primary Care - Windsor.

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Learn more about Windsor

Windsor is well-known for its attractions such as American Precision Museum and Harpoon Brewery. The city has something for everyone including sights like Mt Ascutney State Park and Connecticut River within a scenic setting.

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Check out reviews of Windsor hotels guests love

Align Inn Vermont

10/10 Excellent

"So kind and accommodating "

The Shire Woodstock

10/10 Excellent

"After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!"

The Mountain Inn at Killington

10/10 Excellent

"We had a great weekend stay. Staff was great. We had a nice clean room, the continental breakfast had a great selection and the restaurant was really nice, food was delicious and so very convenient. We really enjoyed sitting by the fire in the lounge type room. And although we didnt bring our dog i was happy to see other dogs around and the fact that everyone is respectful, you wouldn't know that there were dogs staying there if you didn't see them. "

Frequently asked questions

How much does a hotel room cost in Windsor?

You can discover great hotels in Windsor from $80 with properties to suit all budgets and needs. If you're after an affordable hotel in Windsor that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Windsor hotels?

Discover great deals on Windsor hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. And make sure to check out our last-minute deals on Windsor hotels.

Can I book Windsor hotels with free cancellation?

It's easy to book a refundable Windsor hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some top pet-friendly hotels in Windsor?

Consider one of our travelers' favorite pet-friendly hotels in Windsor:

Fat Sheep Farm & Cabins: A farm stay with a guest rating of 9.8 out of 10

You can check "Pet friendly" on the Hotels.com "Amenities" filter in your search to find even more pet-friendly hotels in Windsor.

What are some of the best hotels in Windsor for couples?

Choose a top-rated Windsor romantic hotel and enjoy your couple's getaway. Our travelers love Windsor Mansion Inn, a bed & breakfast with proposal/romance packages as well as in-room champagne service. Use the "Traveler experience" filter in your search and select "Adults only" or "Romantic" to find even more hotels in Windsor for couples on Hotels.com.

What are some of the best Windsor hotels with free parking?

If you're driving, a great Windsor hotel with free parking is a bonus. Our travelers' favorites include:

Fat Sheep Farm & Cabins: A farm stay with an average guest rating of 9.8 out of 10
Windsor Mansion Inn: A bed & breakfast with an average guest rating of 9.2

What are some popular hotels in central Windsor?

If you're looking for hotels in central Windsor, check out Fat Sheep Farm & Cabins and Windsor Mansion Inn. Travelers love Fat Sheep Farm & Cabins for its location, as well as the free parking, terrace and decks/patios this farm stay offers. Windsor Mansion Inn is another popular central bed & breakfast with a bar/lounge, a coffee shop/cafe and a free continental breakfast.

What hotels do travelers like in Windsor?

Guests like Holiday Inn Club Vacations Mount Ascutney Resort by IHG.

Can I book refundable hotels in Windsor?

If you want the flexibility to change your plans to Windsor, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Windsor if I want a vacation home instead of a traditional hotel?

Browse 12 vacation homes on our site. You can also book one of the 6 cabins for your stay.

What will the weather in Windsor be like during my vacation?

July and August are typically the warmest months in Windsor when the average temp is 62°F. January and February are the coldest months when the average temperature is 22°F. July and June are the months with the most rain.

Why should I book my Windsor hotel with Hotels.com?

There are lots of reasons to book your Windsor trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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