Find hotels in Windsor, VA from CA $82

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 17 - May 19

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top 10 Windsor hotels and places to stay

Marina
Smithfield Station
3.0 star property
8.8 out of 10, Excellent, (371)
"Smithfield Station is a quaint hotel right on the water. My room had a balcony overlooking the boat dock. It's a beautiful setting. The hotel staff was pleasant and helpful. Parking was easy. The restaurant is right next door, great food."
The price is CA $209
CA $241 total
includes taxes & fees
May 12 - May 13
Smithfield Station
In-room safe, desk, iron/ironing board, free cribs/infant beds
Hampton Inn Suites Smithfield
2.5 star property
8.8 out of 10, Excellent, (488)
"Staff were very helpful. One of the guests tracked mud into the building, but otherwise rooms and building were very clean and pleasant."
The price is CA $217
CA $243 total
includes taxes & fees
Jun 6 - Jun 7
Hampton Inn Suites Smithfield
Lobby
Stonewood Inn & Suites Carrollton - Smithfield
2.0 star property
5.4 out of 10, (40)
"It is was okayyy.... room and bathroom was clean good "
The price is CA $105
CA $117 total
includes taxes & fees
May 22 - May 23
Stonewood Inn & Suites Carrollton - Smithfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Room
Smithfield Inn
3.5 star property
9.0 out of 10, Wonderful, (56)
"This was our second visit. We had a three room suite that was very comfortable. Our room was over the front porch on Main Street and it still managed to be a peaceful space. We enjoyed a good meal in the restaurant. I would call this a quirky place because on Sunday no staff was present. We didn't know to expect this so missed getting coffee pods for our room. Next time we visit we will plan ahead."
The price is CA $286
CA $320 total
includes taxes & fees
May 16 - May 17
Smithfield Inn
Fridge, microwave, oven, stovetop
The Cracker Jack House: A Military Salute & Arcade!
8.8 out of 10, Excellent, (3)
"From checking in to checking out our stay was absolutely wonderful. You feel so comfortable here. It’s very welcoming. I look forward to visiting again"
The Cracker Jack House: A Military Salute & Arcade!
Microwave, oven, stovetop, dishwasher
Welcome to Carrollton
10.0 out of 10, Exceptional, (5)
"Very comfortable house with large rooms and plenty of space throughout the home. The spaces in the main rooms provided plenty of space for our work meetings and allowed to work in small groups for discussions. Definitely recommend this house for large numbered families or for off-site work related group meetings. Highly recommend if anyone is looking for a quiet and peaceful residence to enjoy, this home in this quiet residential neighborhood would be a great one to consider."
Welcome to Carrollton
Fridge, microwave, stovetop, dishwasher
Spacious Smithfield Home w/ Screened Porch & Yard!
8.0 out of 10, Very good, (1)
"The house was just as expected, little thins missing in kitchen, no cutting board and the grill had to be scrubbed well before use."
Spacious Smithfield Home w/ Screened Porch & Yard!
Don't see what you're looking for?
See all available 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.

More cheap stays in Windsor

Sleep Inn & Suites Chesapeake - Portsmouth

Sleep Inn & Suites Chesapeake - Portsmouth

3280 Western Branch Blvd, Chesapeake, VA
The price is CA $103 per night from May 12 to May 13
CA $103
CA $124 total
includes taxes & fees
May 12 - May 13
6.4/10 (321 reviews)

Windsor Travel Info

Number of hotels
98
Highest price
CA $286
Lowest price
CA $82
Known attractions
Boykin's Tavern and Lake Prince

Frequently asked questions

What's the best place to stay in Windsor?

Sleep Inn & Suites Chesapeake - Portsmouth, located 19.1 mi (30.8 km) from the heart of Windsor, is a top choice for your stay based on our traveler data. Two other options for your trip to the area are Comfort Suites Suffolk - Chesapeake and Hilton Garden Inn Suffolk Riverfront. See all available top hotels, or vacation rentals in Windsor.

What's the top vacation rental that Windsor has to offer?

Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.: Visitors like this Windsor vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! Most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

Where can I learn more about changing or cancelling my trip to Windsor?

To access more information about changing or cancelling your trip to Windsor, click here.

What are some accommodations with pools in Windsor?

Hilton Garden Inn Chesapeake/Suffolk: Features a snack bar, a pool, and free Internet. Hilton Garden Inn Suffolk Riverfront and Courtyard by Marriott Suffolk Chesapeake are a couple of other choices that offer an onsite pool. View all hotels with pools in Windsor.

What's the best place to stay near Norfolk International Airport (ORF)?

Red Roof Inn Virginia Beach - Norfolk Airport is a popular hotel, featuring an outdoor pool and free WiFi. It's located a short 1.6 mi (2.7 km) from Norfolk Intl. Airport. Other good choices within close proximity to the airport include Comfort Inn & Suites Virginia Beach - Norfolk Airport and Americas Best Value Inn Norfolk Airport Area.

What is staying in Windsor like?

Visitors to Windsor are sure to find plenty to explore and enjoy. There are 98 hotels and other accommodations in the surrounding area. Find out more about Windsor.

What should I do while I'm visiting Windsor?

Places to visit in the wider area include Planters Peanut Center, Lake Prince, and Suffolk Center for Cultural Arts. You'll also find Windsor Castle Park and Smithfield Farmers Market in the area. Check out what more to see and do in Expedia's Windsor guide.

What's the weather like in Windsor?

The hottest months are usually July and August with an average temp of 76°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Windsor is 52 inches.

Recent Reviews in Windsor
Expedia verified reviews

Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel

Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel

5/5 Excellent
"Nice"
A verified traveller stayed at Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel
Posted 3 days ago
Holiday Inn Express Hotel & Suites Suffolk, an IHG Hotel