Windsor, VA

Travel Guide

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
$93 nightly
The price is $108 total per night from Oct 11 to Oct 12
$108 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Comfort Suites Airport
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
$93 nightly
The price is $110 total per night from Sep 27 to Sep 28
$110 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Norfolk. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Wyndham Garden Norfolk Downtown
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Fully refundable
$210 nightly
The price is $231 total per night from Oct 4 to Oct 5
$231 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Kingsmill Resort
See all 706 properties in Windsor
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.
stayAPT Suites Hampton

stayAPT Suites Hampton

2.5 out of 5
2122 Hartford Rd Hampton VA
Book a stay at this business-friendly aparthotel in Hampton. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Hampton Coliseum and ...
10/10 Exceptional! (15 reviews)
"Property is brand new and I thought quite nice. Very convenient location too"

Reviewed on Sep 14, 2026

stayAPT Suites Hampton
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

3.5 out of 5
5961 Harbour View Blvd Suffolk VA
Book a stay at this business-friendly aparthotel in Suffolk. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Riverfront Golf Club and ...
stayAPT Suites Suffolk-Chesapeake
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Portsmouth VA
Stay at this vacation home in Portsmouth. Enjoy free WiFi, a garden, and patios. Popular attractions Waterside District and Portsmouth City Park are located ...
8.8/10 Excellent! (12 reviews)
"Small but very cozy. Clean with no complaints. Host was friendly. Says it has stove but has hot plate. Would still recommend"

Reviewed on Sep 16, 2026

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
See all properties in Windsor
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.
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Frequently asked questions

Is Windsor worth visiting?
Windsor is worth visiting for its local dining scene, which offers delicious North American and Italian cuisine. Travelers can also explore standout attractions such as the historic Boykin's Tavern, providing a blend of culinary delights and cultural experiences.
When is the best time to visit Windsor?
The best time to visit Windsor is from May through July, when the destination is most popular. For travelers seeking fewer crowds and better value, the quieter months of November through January are a good option, offering a more relaxed experience.
What is Windsor known for?
Windsor is known for Boykin's Tavern, a prominent local institution that offers a glimpse into the area's heritage. Travelers can also enjoy the destination's North American food culture, providing a taste of regional culinary traditions.
What is a good itinerary length for Windsor?
A good itinerary length for Windsor is one day to visit Boykin's Tavern. An extended stay of two days would allow travelers to further explore the area and enjoy local dining, with options including North American, Italian, and Asian cuisine.
What are the top things to do in and around Windsor?
In Windsor, travelers can visit Boykin's Tavern, a historic landmark and point of interest.
What cuisines can you find in Windsor?
In Windsor you can find Thai cuisine, with dishes like Pad Thai, Green Curry, and Tom Yum Soup. Travelers can also enjoy North American comfort food, Italian pasta dishes, and Mexican favorites such as tacos and burritos, alongside other Asian and European options.
Can I book a refundable hotel in Windsor?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Windsor by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Windsor with Expedia?
Expedia makes it easier to plan your Windsor trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Windsor?
The best choice depends on your travel style. Hotels in Windsor can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Windsor trip on Expedia?
Once you've booked your Windsor trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Windsor trip?
Expedia offers customer support before, during, and after your Windsor trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Windsor?
If it's your first trip to Windsor, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Windsor hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Windsor hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Windsor

A person rowing a boat on a misty lake with a tree and a sunlit sky in the background.

Suffolk

A river curving through a landscape with dry grass fields, a dock with boats, and houses along the riverbank.

Smithfield

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