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.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $547, price is now $450 per person
$450
per person
Oct 5 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Enjoy the gym and perks like free self parking.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $654, price is now $497 per person
$497
per person
Oct 19 - Oct 23
found 16 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $705, price is now $547 per person
$547
per person
Oct 9 - Oct 12
found 8 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.
Saltaire Cottages

Saltaire Cottages

2.5 out of 5
Price was $832, price is now $671 per person
$671
per person
Oct 5 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Norfolk (ORF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a picnic area are also on offer.
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 $880, price is now $733 per person
$733
per person
Oct 9 - Oct 12
found 8 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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.

Top Windsor hotels deals

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
$88 nightly
The price is $105 total per night
$105 total
Sep 7 - Sep 8
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
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Free Cancellation
$101 nightly
The price is $117 total per night
$117 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Free Cancellation
Reserve now, pay when you stay
$258 nightly
The price is $285 total per night
$285 total
Sep 1 - Sep 2
Total with taxes and fees
This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.
Pool
Hot Tub
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
$98 nightly
The price is $114 total per night
$114 total
Sep 20 - Sep 21
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
Country Inn & Suites by Radisson, Hampton Coliseum

Country Inn & Suites by Radisson, Hampton Coliseum

3 out of 5
1917 Coliseum Dr Hampton VA
Free Cancellation
$94 nightly
The price is $111 total per night
$111 total
Sep 14 - Sep 15
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like daily breakfast and free self parking.
Pool
Breakfast included
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
$122 nightly
The price is $144 total per night
$144 total
Aug 30 - Aug 31
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
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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.

Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)
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.
See properties

Frequently asked questions

How much are vacation packages to Windsor?
Starting as low as $450, 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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