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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $630, price is now $509 per person
$509
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Price was $648, price is now $518 per person
$518
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the outdoor tennis court and perks like free WiFi. There's a seasonal outdoor pool on site, and a 24-hour front desk and a rooftop terrace are also provided.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 out of 5
Northeast Virginia Beach
Price was $679, price is now $568 per person
$568
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Norfolk (ORF)
This aparthotel 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.
Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Price was $664, price is now $561 per person
$561
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Norfolk (ORF)
This condo resort features an indoor pool, a gym, and a restaurant. Enjoy the sauna and perks like free self parking and free WiFi. A picnic area and laundry facilities are also provided.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was $643, price is now $549 per person
$549
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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 business center, laundry facilities, and free newspapers 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.
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 7 - Oct 8
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.
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.
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 $509, 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