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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $724, price is now $469 per person
$469
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, express check-out, and laundry facilities are also on offer.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,657, price is now $1,563 per person
$1,563
per person
Apr 9 - Apr 13
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $958, price is now $682 per person
$682
per person
Apr 9 - Apr 13
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Norfolk (ORF)
This hotel features a hot tub and a sauna. Free self parking and concierge services are also offered on site.
The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,079, price is now $770 per person
$770
per person
Apr 9 - Apr 13
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Enjoy the 2 hot tubs and perks like free WiFi.
Hilton Vacation Club Beachwoods Kitty Hawk

Hilton Vacation Club Beachwoods Kitty Hawk

4 out of 5
Sea Scape
Price was $722, price is now $529 per person
$529
per person
Apr 9 - Apr 13
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Bring the family and enjoy the lazy river, children's pool, and waterslide. Enjoy the outdoor tennis court and perks like free self parking and free WiFi.

Top Windsor hotels deals

Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $149 total per night
$149 total
Jan 29 - Jan 30
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
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $105 total per night
$105 total
Jan 21 - Jan 22
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
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
$79 nightly
The price is $94 total per night
$94 total
Feb 8 - Feb 9
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
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
$107 nightly
The price is $126 total per night
$126 total
Jan 25 - Jan 26
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
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
Jan 25 - Jan 26
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
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
100 East Main Street Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$174 nightly
The price is $203 total per night
$203 total
Jan 29 - Jan 30
Total with taxes and fees
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.
Pool
Restaurant
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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.

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 $469, 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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