Where can I find cheap hotels in Windsor?

At Travelocity you'll find really nice hotels in Windsor at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windsor rather than in Windsor. We may find you even better rates, too.

How do I find the best Windsor hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Windsor then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Windsor?

The cheapest hotel in Windsor is $109. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Windsor?

There are 1865 hotels in Windsor on Travelocity.

When is the best time to visit Windsor?

If you want the joy of a fun-filled trip in peak season, visit Windsor during . If you'd prefer the peace of off-season, book a stay during quieter months, such as .

When is the cheapest time to stay in Windsor?

Based on historic data is usually the cheapest month to visit Windsor. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Windsor?

There are multiple hotels in Windsor that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windsor. We have plenty of kid-friendly hotels in Windsor to choose from on Travelocity!

How do I cancel my hotel booking in Windsor on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Windsor, Vermont Hotels from $109 - Hotel Deals

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Most frequently booked Windsor hotels

Windsor Mansion Inn

153 Pembroke Road, Windsor, VT, 05089

2.57 mi from city center

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A bar/lounge and a coffee shop are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

Free WiFi

Breakfast included

Fat Sheep Farm & Cabins

122 Best Rd, Windsor, VT, 05089

3.39 mi from city center

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This farm stay doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a picnic area are also on offer.

Free WiFi

Parking included

Snapdragon Inn

26 Main Street, Windsor, VT, 05089

3.12 mi from city center

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This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Free breakfast is served. A terrace, a garden, and a picnic area are also on offer.

Free WiFi

Breakfast included

Beautiful home offering privacy on 7 acres with private pond

Windsor, VT

3.11 mi from city center

This vacation home includes a garden and barbecue grills.

Free WiFi

Kitchen

Largest Colonial Revival Mansion less than 15 minutes to Woodstock

Windsor, VT

2.59 mi from city center

This property features barbecue grills.

Free WiFi

Air conditioning

The Mountain Inn at Killington

47 Old Mill Rd, Killington, VT, 05751

Free Cancellation

Reserve now, pay when you stay

19.95 mi from city center

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Free WiFi

Fireside Inn & Suites West Lebanon

25 Airport Road, West Lebanon, NH, 03784

11.38 mi from city center

This hotel features an indoor pool, a spa tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Free WiFi

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd, Killington, VT, 05751

Free Cancellation

Reserve now, pay when you stay

19.79 mi from city center

This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free ski shuttle. Take advantage of ski passes and ski storage on site. Families will appreciate the arcade/game room and onsite laundry facilities.

Free WiFi

Parking included

North Star Lodge and Resort

78 Weathervane Dr, Killington, VT, 05751

Free Cancellation

Reserve now, pay when you stay

20.56 mi from city center

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Free WiFi

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See all available properties in Windsor

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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.

Top hotels in Windsor for Extended Stay

Winterplace at Okemo
77 Okemo Ridge Rd, Ludlow, VT, 05149
4/5 Very Good! (2 reviews)
Winterplace at Okemo
Solitude Village at Okemo
77 Okemo Ridge Rd, Ludlow, VT, 05149
Solitude Village at Okemo
The Woods Resort And Spa - GetAway
53 Woods Lane, Killington, VT, 05751
The Woods Resort And Spa - GetAway
Fall Line Condominiums
786 E Mountain Road, Killington, VT, 05751
Fall Line Condominiums

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.

Windsor Hotel & Travel Guide\n

Thinking about exploring Central Vermont- Killington? To experience it as the locals do, reserve places to base your trip that are within an easy drive from the excitement of Windsor. Travelocity's hotel guide presently has listed 5 accommodations in and around the CBD district and surrounds of Windsor.

The Holiday Inn Club Vacations Ascutney Mountain Resort is the nearest hotel to the downtown area of Windsor and it's simply a brief drive away.

13 miles (21 kilometers) from downtown Windsor, you will find the Castle Hill Resort And Spa. Alternatively, the Inn at Clearwater Pond can be found approximately 9 miles (15 kilometers) away. The Woodstock Inn & Resort along with the Mountain Lodge at Okemo Mountain Resort are some other Travelocity-listed accommodation options in Windsor.

Keen on discovering even more of the forests and mountains that this area features? What if you take some time in nearby places in Central Vermont? Take part in snowboarding, skiing and cross-country skiing or venture out to see the area's diverse cultural and scenic sights. Comfortable Travelocity-listed hotels are located nearby.

20 miles (32 kilometers) to the northwest of Windsor, you can find Killington, which is where you can visit Killington Ski Resort and Green Mountain National Golf Course. The Killington Grand Resort Hotel and Mountain Green Ski & Golf Resort are just a handful of the Travelocity hotel options in Killington. Or, you could stay in Rutland, 30 miles (45 kilometers) west of Windsor, where you can choose between the Hampton Inn Rutland and Holiday Inn Rutland-Killington Area. The Pine Hill Park and Vermont State Fairgrounds are a couple of the most popular sites to explore in Rutland.

Just because you are on a break, should not mean that you can't enjoy your love for a day at the stadium. Find Verizon Wireless Arena 60 miles (98 kilometers) to the southeast of Windsor. And travelers wishing to sleep close to the action can take their choice from the Hilton Garden Inn Manchester Downtown or the Radisson Hotel Manchester Downtown.

If you are traveling via Lebanon Municipal Airport and would like to stay nearby, try Hampton Inn White River Junction or Fireside Inn & Suites West Lebanon.

Frequently asked questions

Family vacations are where lifelong memories are made, but it’s no secret that traveling with youngsters can be tricky. These kid-friendly Windsor hotels come with perks designed to keep travelers of all ages relaxed and happy: Windsor Mansion Inn will help make your adventure the best one yet. It comes with a range of conveniences geared toward families, such as a cafe and a firepit. Also check out the deals at Beautiful home offering privacy on 7 acres with sledding hill and private pond. It offers a king bed, a travel crib and ample opportunities to hang out as a family.

Windsor has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windsor for you!

Because we have the top hotels in Windsor! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

Recent Windsor hotel reviews by fellow wanderers

The Mountain Inn at Killington
5 out of 5
Posted 4 months ago
travelocity Verified Review
"Beautiful view, friendly staff and great dinners."
A verified traveler from Hopewell Junctio stayed at The Mountain Inn at Killington
The Mountain Inn at Killington
Windsor Mansion Inn
5 out of 5
Posted 7 months ago
travelocity Verified Review
"This is a lovely mansion [with great history] on a hill in Vermont. It has a welcoming, knowledgeable and accommodating host, cozy rooms and good breakfasts. We had the standard continental breakfast our first morning, consisting of oatmeal with bananas, a small ramekin of yogurt with blueberries and several small chocolate croissants. We upgraded the second morning and were treated to a delicious baked French toast and local sausages; orange juice was standard with each meal. An extra touch that made me very happy - and a bit relieved - was that they had a makeup remover pad and a dark washcloth in the bathroom! (I usually bring my own washcloth, so as not to mess up the typical white ones in most hotels, but I had neglected to put it in my suitcase so didn't have it with me.) Being an older home, it does not appear to be conducive to individuals with mobility issues. To my knowledge, most guest rooms are on the second or third floor, accessible by stairs (I did not see an elevator). Their COVID protocols required masks to be worn outside of our guest room, hands to be sanitized prior to using the coffee station and they limited seating in dining areas to allow for distancing. It was a perfect home base to explore the area during a getaway weekend. I hope to return soon!"
A verified traveler from MILFORD stayed at Windsor Mansion Inn
Windsor Mansion Inn
North Star Lodge and Resort
5 out of 5
Posted 8 months ago
travelocity Verified Review
"I booked a suite and it was very clean and spacious. The jacuzzi is in the king bed room and it’s big and like new. Checking in and out was too easy. I would recommend this hotel. Thanks "
A verified traveler stayed at North Star Lodge and Resort
North Star Lodge and Resort
Killington Mountain Lodge, Tapestry Collection by Hilton
3 out of 5
Posted 11 months ago
travelocity Verified Review
"This property is undergoing construction and the pool is not in use. Th breakfast is coffee and granola bars, and the rooms have visible damage. You can tell they are not putting money into the up keep of rooms. Very disappointing. "
A verified traveler stayed at Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
Fireside Inn & Suites West Lebanon
5 out of 5
Posted 11 months ago
travelocity Verified Review
"The outside looks terrible as you drive up but then the inside looks wonderful. It’s a nice surprise. Rooms are nice, could use updating and getting rid of the old carpeting. Beds are super comfy. I think the no daily housekeeping should be over! But the sit down,served breakfast was a nice surprise. "
A verified traveler stayed at Fireside Inn & Suites West Lebanon
Fireside Inn & Suites West Lebanon
Best Western West Lebanon-Hanover Hotel
5 out of 5
Posted 11 months ago
travelocity Verified Review
"All ok"
A verified traveler stayed at Best Western West Lebanon-Hanover Hotel
Best Western West Lebanon-Hanover Hotel