Book Hotels in Windsor, Virginia

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Check hotel availability in Windsor

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Dec 1 - Dec 2
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Dec 2 - Dec 4
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Dec 9 - Dec 11

Most frequently booked Windsor hotels

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

2.5 out of 5
2122 Jolliff Rd, Chesapeake, VA, 23321
Free Cancellation
Reserve now, pay when you stay
16.96 mi from city center
The price is $84 per night
$84
per night
Dec 9 - Dec 10
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free Internet in public areas. There's a gym on site, and a 24-hour front desk and a picnic area are also provided.
Free WiFi
Breakfast included
Holiday Inn Express Hotel & Suites Chesapeake, an IHG Hotel

Holiday Inn Express Hotel & Suites Chesapeake, an IHG Hotel

2.5 out of 5
2436 Gum Rd, Chesapeake, VA, 23321
Free Cancellation
17.79 mi from city center
The price is $94 per night
$94
per night
Dec 11 - Dec 12
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the spa tub and free perks like buffet breakfast and free self parking.
Pool
Free WiFi
Hilton Garden Inn Suffolk Riverfront

Hilton Garden Inn Suffolk Riverfront

3 out of 5
100 E Constance Rd, Suffolk, VA, 23434
Free Cancellation
Reserve now, pay when you stay
10.68 mi from city center
The price is $93 per night
$93
per night
Dec 9 - Dec 10
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms, as well as the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Free WiFi
Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel

Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel

2.5 out of 5
1018 Centerbrooke Ln, Suffolk, VA, 23434
Free Cancellation
9.59 mi from city center
The price is $116 per night
$116
per night
Dec 8 - Dec 9
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Free WiFi
Hampton Inn & Suites Chesapeake-Square Mall

Hampton Inn & Suites Chesapeake-Square Mall

2.5 out of 5
4449 Peek Trail, Chesapeake, VA, 23321
Free Cancellation
Reserve now, pay when you stay
18.03 mi from city center
The price is $101 per night
$101
per night
Dec 16 - Dec 17
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and Internet in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Free WiFi
Breakfast included
Courtyard by Marriott Suffolk Chesapeake

Courtyard by Marriott Suffolk Chesapeake

3 out of 5
8060 Harbour View Blvd, Suffolk, VA, 23435
Free Cancellation
Reserve now, pay when you stay
18.46 mi from city center
The price is $105 per night
$105
per night
Dec 15 - Dec 16
This hotel features a restaurant, an indoor pool, and a bar/lounge. 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
Comfort Suites Suffolk - Chesapeake

Comfort Suites Suffolk - Chesapeake

2.5 out of 5
5409 Plummer Blvd, Suffolk, VA, 23435
Free Cancellation
Reserve now, pay when you stay
17.23 mi from city center
The price is $98 per night
$98
per night
Dec 18 - Dec 19
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free Internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Free WiFi
Breakfast included
Sleep Inn & Suites Chesapeake - Portsmouth

Sleep Inn & Suites Chesapeake - Portsmouth

2.5 out of 5
3280 Western Branch Blvd, Chesapeake, VA, 23321
Free Cancellation
Reserve now, pay when you stay
19.13 mi from city center
The price is $67 per night
$67
per night
Dec 25 - Dec 26
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Free WiFi
Hilton Garden Inn Chesapeake/Suffolk

Hilton Garden Inn Chesapeake/Suffolk

3 out of 5
5921 Harbour View Blvd, Suffolk, VA, 23435
Free Cancellation
Reserve now, pay when you stay
17.88 mi from city center
The price is $135 per night
$135
per night
Dec 9 - Dec 10
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a snack bar/deli are also offered.
Pool
Free WiFi
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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.

Seize your some day

Cheap Hotels in Windsor

Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Windsor. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.

Allow us here at Travelocity to pair you with up Windsor hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Windsor that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save $$$. It’s time to explore a new city, and break out of your routine.

Frequently asked questions

What are the top kid-friendly hotels in Windsor?
Family trips are where the best memories are made, but it’s no secret that traveling with little ones can be stressful. These kid-friendly Windsor hotels come with perks designed to keep adventurers of all ages comfortable and happy: Travelodge by Wyndham Suffolk will help make your vacation the most memorable one yet. It features an assortment of nice little touches, such as laundry facilities and a swimming pool. Quality Inn & Suites is also a hit with families. After a long day of exploring Windsor, return to your comfy room and amenities like a swimming pool and a fridge.
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 $67. 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 66 hotels in Windsor on Travelocity.
What are the best hotels in Windsor?
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!
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!
Why book a hotel in Windsor through Travelocity?
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!
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.

Recent Windsor hotel reviews by fellow wanderers

  • Hampton Inn & Suites Chesapeake-Square Mall

    Hampton Inn & Suites Chesapeake-Square Mall

    5 out of 5
    Posted 4 days ago
    travelocity Verified Review
    "The room was clean, the staff was very friendly and there are many restaurants nearby."
    A verified traveler stayed at Hampton Inn & Suites Chesapeake-Square Mall
    Hampton Inn & Suites Chesapeake-Square Mall