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.
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 $751, price is now $550 per person
$550
per person
Mar 15 - Mar 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) 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.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $1,836, price is now $1,050 per person
$1,050
per person
Feb 25 - Feb 28
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $779, price is now $559 per person
$559
per person
Mar 15 - Mar 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) 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.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier
Price was $765, price is now $573 per person
$573
per person
Mar 15 - Mar 21
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, express check-in, and express check-out are also on offer.
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $1,637, price is now $1,231 per person
$1,231
per person
Mar 15 - Mar 21
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A snack bar/deli, express check-in, and express check-out are also on offer.

Top Windsor hotels deals

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 11 - Jan 12
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
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
$92 nightly
The price is $108 total per night
$108 total
Jan 14 - Jan 15
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
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 11 - Jan 12
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
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
$77 nightly
The price is $91 total per night
$91 total
Jan 25 - Jan 26
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 11 - Jan 12
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
Courtyard by Marriott Norfolk Downtown

Courtyard by Marriott Norfolk Downtown

3 out of 5
520 Plume street Norfolk VA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $103 total per night
$103 total
Feb 1 - Feb 2
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 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
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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 $550, 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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