Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
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 $449, price is now $372 per person
$372
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Sioux Falls (FSD) 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.
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $724, price is now $585 per person
$585
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Norfolk (ORF)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Price was $655, price is now $533 per person
$533
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Norfolk (ORF)
This hotel features 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and convenience store.
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Northwest
Price was $682, price is now $569 per person
$569
per person
Nov 9 - Nov 15
found 6 hours ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a lobby fireplace are also offered.
Coastal Hotel and Suites Virginia Beach Oceanfront

Coastal Hotel and Suites Virginia Beach Oceanfront

2.5 out of 5
Northeast Virginia Beach
Price was $520, price is now $437 per person
$437
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Sioux Falls (FSD) to Norfolk (ORF)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, express check-out, and laundry facilities are also on offer.

Top Windsor hotels deals

Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
1905 Coliseum Dr, Hampton, VA
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $110 total per night
$110 total
Nov 2 - Nov 3
Total with taxes and fees
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 free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue, Norfolk, VA
Get rates
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
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St, Norfolk, VA
$135 nightly
The price is $159 total per night
$159 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Free WiFi
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive, Hampton, VA
$97 nightly
The price is $113 total per night
$113 total
Oct 9 - Oct 10
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
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $95 total per night
$95 total
Nov 2 - Nov 3
Total with taxes and fees
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 full breakfast and free self parking.
Pool
Breakfast included
Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

3 out of 5
401 Butler Farm Rd, Hampton, VA
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $112 total per night
$112 total
Nov 2 - Nov 3
Total with taxes and fees
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the laundry service.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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.

Popular places to visit

Boykin's Tavern

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.

Boykin's Tavern

Frequently asked questions

How much are vacation packages to Windsor?
Starting as low as $372, 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

Browse Windsor vacation photos for more inspiration