Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was $588, price is now $474 per person
$474
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Norfolk (ORF)
This aparthotel features an indoor pool, a gym, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.
The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was $812, price is now $578 per person
$578
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Norfolk (ORF)
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A safe deposit box is provided and the front desk is staffed around-the-clock.
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was $835, price is now $610 per person
$610
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
Northwest
Price was $718, price is now $570 per person
$570
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Price was $1,000, price is now $794 per person
$794
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Norfolk (ORF)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Top Windsor hotels deals

Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $105 total per night
$105 total
Sep 7 - Sep 8
Total with taxes and fees
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. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Pet friendly
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Free Cancellation
$101 nightly
The price is $117 total per night
$117 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. 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
Breakfast included
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Free Cancellation
Reserve now, pay when you stay
$258 nightly
The price is $285 total per night
$285 total
Sep 1 - Sep 2
Total with taxes and fees
This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.
Pool
Hot Tub
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $114 total per night
$114 total
Sep 20 - Sep 21
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the 24-hour gym and free continental breakfast each morning.
Pool
Breakfast included
Country Inn & Suites by Radisson, Hampton Coliseum

Country Inn & Suites by Radisson, Hampton Coliseum

3 out of 5
1917 Coliseum Dr Hampton VA
Free Cancellation
$94 nightly
The price is $111 total per night
$111 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like daily breakfast and free self parking.
Pool
Breakfast included
Sheraton Norfolk Waterside Hotel

Sheraton Norfolk Waterside Hotel

3.5 out of 5
777 Waterside Dr Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $144 total per night
$144 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Pool
Pet friendly
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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.

Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)
You can study the exhibits at Boykin's Tavern, a museum with a storied past, during your trip to Isle of Wight. Discover the area's live music and churches.
See properties

Frequently asked questions

How much are vacation packages to Windsor?
Starting as low as $474, hotel and flight packages are a superb way to stretch your vacation budget. Watch out Windsor — here you come!
Where can I get the best vacation package deals for Windsor?
Scoring the best package deal to Windsor is a piece of cake with Travelocity. With access to 400 partner airlines and 1,000,000 properties around the world, you'll have loads of choice when selecting your hotels and flights.
Why should I book my Windsor vacation bundle via Travelocity?
With fantastic service, 24/7 customer support and some of the most idyllic escapes imaginable, you'll never wander alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Windsor car rental if I combine it with my hotel or flight?
You sure can — bundle your hotel, flight and car into a Windsor vacation package and you'll save tons. With so many things to do in the Windsor area, having your own set of wheels will make exploring easy. Once you're behind the wheel, put the stereo on and find your way to Water Country USA, a must-see attraction around 30 mi from Windsor.
Which airport is best for Windsor?
Richmond Intl. Airport (RIC) (60 mi away from the downtown area), Norfolk Intl. Airport (ORF) (30 mi away from central Windsor) and Newport News - Williamsburg Intl. Airport (PHF) (25 mi away from central Windsor) are all top options for Windsor.

Photos of local treasures

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