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 $585, price is now $404 per person
$404
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $914, price is now $596 per person
$596
per person
Sep 25 - Sep 30
found 8 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) to Norfolk (ORF)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the playground and barbecue grills. There's an outdoor pool on site, and a terrace and a picnic area are also provided.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $4,323, price is now $2,923 per person
$2,923
per person
Sep 25 - Sep 30
found 8 hours ago
Roundtrip non-stop flight included
Fort Wayne (FWA) 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.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Price was $695, price is now $504 per person
$504
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) 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.
Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Price was $676, price is now $492 per person
$492
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.

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
$135 nightly
The price is $159 total per night
$159 total
Sep 1 - Sep 2
Total includes 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.
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
$94 nightly
The price is $112 total per night
$112 total
Sep 4 - Sep 5
Total includes 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.
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
$88 nightly
The price is $104 total per night
$104 total
Sep 1 - Sep 2
Total includes 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
Quality Inn & Suites Olde Town

Quality Inn & Suites Olde Town

2.5 out of 5
347 Effingham St, Portsmouth, VA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $128 total per night
$128 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Parking included
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
$101 nightly
The price is $118 total per night
$118 total
Sep 1 - Sep 2
Total includes 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
The Landing at Hampton Marina, Tapestry Collection by Hilton

The Landing at Hampton Marina, Tapestry Collection by Hilton

3.5 out of 5
700 Settlers Landing Rd., Hampton, VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $128 total per night
$128 total
Sep 7 - Sep 8
Total includes taxes and fees
A marina, 4 restaurants, and a gym are all featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
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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 $404, 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