Windsor Holiday Rentals, Virginia: Private House Rentals

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Our top choices for Windsor hotels

A hotel lobby with multiple dining tables and chairs, a fireplace, and a blue wall with framed pictures.

A hotel room with a dining table, chairs, a sofa, a TV, and a fireplace.

A hotel room with a large bed, two bedside lamps, a chair, and a desk.

A spacious lobby with a reception desk, a staircase, and a glass door entrance.

1. Holiday Inn Express Hotel & Suites Suffolk by IHG

Suffolk

Gary

฿3,290

฿3,784 total

includes taxes & fees

12 Nov - 13 Nov

A conference room with a long table, red upholstered chairs, and orange pendant lights.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a blue tiled wall.

A Hampton Inn hotel with a brick facade, multiple windows, and a clear entrance.

A hotel room with a wooden floor, a bed, a desk, a chair, a bathroom with a shower, and a mirror.

2. Hampton Inn Suffolk

Suffolk

฿3,395

฿3,904 total

includes taxes & fees

1 Nov - 2 Nov

A large hotel with a central courtyard, multiple floors, and a well-lit entrance.

A modern bar area with stainless steel appliances, a wine rack, and a seating area with a wooden ceiling.

A spacious hotel lobby with a red and white carpet, large windows, and a chandelier.

A covered outdoor seating area with brick flooring, white columns, and blue furniture.

3. Hilton Garden Inn Suffolk Riverfront

Suffolk

Zina B

฿3,966

฿4,555 total

includes taxes & fees

11 Nov - 12 Nov

A modern hotel lobby with a central bar area, seating arrangements, and a decorative light fixture.

A hotel room with a bed, bedside tables, a desk, a chair, and a bathroom visible through an open door.

A hotel reception area with a wooden reception desk, a large yellow hanging light fixture, a framed picture on the wall, and a coffee station with multiple drink dispensers.

A bathroom with a shower, a sink with a mirror, and a framed picture on the wall.

4. Hampton Inn Suites Smithfield

Smithfield

Laurence

฿3,402

฿3,810 total

includes taxes & fees

1 Nov - 2 Nov

A modern reception area with a counter, a sign reading 'HOME,' and a display of green apples.

A modern hotel lobby with a reception desk, a snack bar, and a seating area.

5. Home2 Suites By Hilton Suffolk

Suffolk

Amber

฿4,544

฿5,214 total

includes taxes & fees

8 Nov - 9 Nov

A modern hotel room with a bed, bedside table, and a small desk with a mirror.

A bathroom with a granite countertop sink, a toilet, and a shower with a glass door.

A building with a brick facade, a green roof, and a covered entrance with a staircase.

A hotel room with two single beds, a desk, a mirror, a window, and a bathroom.

6. Brentwood Inn & Suites

Suffolk

Steve

฿2,623

฿3,024 total

includes taxes & fees

11 Nov - 12 Nov

A waterfront property with a dock, a tower, and a house.

A spacious living room with hardwood floors, a central coffee table, and a large rug.

A waterfront hotel with multiple balconies, a dock with boats, and a clear sky.

A pool area with white lounge chairs and a building with a green roof and a tower.

7. Smithfield Station

Smithfield

Jason

฿5,518

฿6,366 total

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with a central seating area, a reception desk, and multiple levels with balconies.

A spacious indoor dining area with multiple tables and chairs, a large central tree, and a kitchen in the background.

A gym with treadmills, a stationary bike, and a bench press.

8. Embassy Suites by Hilton Hampton Convention Center

Coliseum Central

Chianti

฿3,275

฿3,834 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with wicker furniture, a stone wall, and string lights.

A modern restaurant with a bar area, multiple seating options including round tables and booths, and a view of the outdoors through large windows.

A modern Hyatt Place hotel with a covered entrance, well-maintained landscaping, and a clear sky at dusk.

A modern lounge area with leather sofas, tables, and a stone accent wall.

9. Hyatt Place Hampton Convention Center

Coliseum Central

Dorian

฿3,565

฿4,167 total

includes taxes & fees

20 Oct - 21 Oct

A modern bar area with a refrigerated drink display, a long counter with stools, and a menu board above.

A modern living room with a fireplace, comfortable seating, and a carpeted floor.

A modern living room with a sofa set, armchairs, a coffee table, and a flat-screen TV mounted on the wall.

A modern hotel lobby with a large digital display, comfortable seating, and a well-lit interior.

10. Courtyard by Marriott Suffolk Chesapeake

Suffolk

Ramzia

฿2,954

฿3,401 total

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with clear water, surrounded by a gym area with exercise equipment.

A hotel reception area with two reception desks, a chalkboard with a message, and a Holiday Inn Express sign.

A modern conference room with a large table, chairs, and a computer setup.

A multi-story hotel with a covered entrance and a parking lot.

11. Holiday Inn Express & Suites Newport News by IHG

Newport News

Eva

฿2,820

฿3,276 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio area with stone walls, outdoor furniture, and string lights.

A reception area with wooden reception desks, a wall with a vertical garden, and a ceiling with recessed lighting.

A Fairfield by Marriott hotel with a modern design, a covered entrance, and outdoor seating area.

A modern hotel lobby with a central bar area, seating arrangements, and large windows providing natural light.

12. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

Darrell

฿3,000

฿3,517 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a flat-screen TV mounted on the wall, a desk with a chair, a microwave, and an air conditioning unit.

A Red Roof Inn reception area with a counter, ATM, and seating area.

A Red Roof Inn with a parking lot in front.

A Red Roof Inn lobby with two leather chairs, an ATM, and a stone wall.

13. Red Roof Inn Suffolk

Suffolk

Tracy

฿2,621

฿3,105 total

includes taxes & fees

15 Oct - 16 Oct

A modern restaurant with hexagonal patterned flooring, wooden tables and chairs, a central bar area, and a fireplace.

A reception area with a blue sofa, a tufted bench, a reception desk, and a patterned floor.

A modern lounge area with a fireplace, seating, and a ceiling light fixture.

14. Comfort Suites Airport

Central Newport News

Samantha

฿3,110

฿3,610 total

includes taxes & fees

3 Nov - 4 Nov

A hotel lobby with multiple seating areas, including tables and chairs, and a large clock on the wall.

A hotel room with a desk, chair, ottoman, air conditioning unit, and a framed picture on the wall.

A swimming pool with clear water, surrounded by lounge chairs and a safety railing.

A neatly made bed with white linens, two bedside lamps, a wooden bench, and a framed picture on the wall.

15. Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

฿2,725

฿3,201 total

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with clear water, surrounded by a tiled floor, and equipped with a pool ladder.

A spacious lobby with a central kiosk, large potted plants, and modern pendant lighting.

A kitchenette with a microwave, coffee maker, and a dishwasher.

16. Hilton Garden Inn Chesapeake/Suffolk

Suffolk

Anautica

฿3,551

฿4,081 total

includes taxes & fees

25 Oct - 26 Oct

A modern interior with a black leather sofa, green and yellow chairs, and a patterned floor.

A marina with several boats docked, a waterfront restaurant named 'WaterSide', and modern buildings in the background.

A spacious lobby with a central walkway, seating areas, and large windows offering views of the cityscape.

A multi-level interior with an escalator connecting floors, modern lighting, and a central seating area with tables and chairs.

17. Hilton Norfolk The Main

Downtown Norfolk

Francis

฿8,531

฿10,039 total

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a modern facade, a prominent entrance with a covered area, and a sign indicating it is a Marriott property.

A modern hotel lobby with seating areas, a bar, and a television displaying a sports event.

A hotel room with a bed, bedside lamp, nightstand, and a view of the kitchen area.

A modern kitchen with a refrigerator, microwave, and coffee maker. There is a dining area with a table and chairs, and a small bookshelf.

18. Towneplace Suites By Marriott Newport News Airport

Central Newport News

Carol

฿3,262

฿3,721 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with a geometric design.

A marina with several yachts docked, a large illuminated building in the background, and a Ferris wheel.

A modern outdoor seating area with sofas, chairs, and a round table, surrounded by potted plants and a view of a building with a blue roof.

A bar area with a marble countertop, bar stools, and a variety of bottles and glasses.

19. Norfolk Waterside Marriott

Downtown Norfolk

Shakenya

฿4,532

฿5,346 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk with a chair, a sofa, a TV, and a window with curtains.

A modern hotel lobby with a reception desk, seating area, and a television mounted on the wall.

A multi-story hotel with a prominent entrance and parking area.

A reception area with a counter, seating, and a coffee machine.

20. Candlewood Suites Chesapeake/Suffolk by IHG

Western Branch North

Lamont

฿2,724

฿3,200 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)

This 18th-century tavern showcases original colonial panelling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.

See properties

Top Windsor Hotel Reviews

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent

"It a beautiful place but the floor was fillthy."

Sonesta Simply Suites Hampton

8/10 Good

"it was clean and served my purposes"

Sheraton Norfolk Waterside Hotel

8/10 Good

"Room is very clean couldn't ask for a better location to stay very close to the cruise terminal"

Holiday Inn Express Hampton - Coliseum Central by IHG

10/10 Excellent

"Experience was wonderful and the staff was excellent!"

Courtyard by Marriott Newport News Airport

10/10 Excellent

"It was so easy to check in and out. the staff took care of all our needs. Would recommend to anyone looking for a place to stay that is clean and accommodating with the amenities needed for your stay."

Wyndham Garden Norfolk Downtown

8/10 Good

"The room was spacious with all usual amenities. The bathroom was good size and pleasant. Over all the location of the hotel is good, close ( walking distances) to Chrysler museum, restaurants and center of city ."

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent

"It was quiet and clean. Good location!"

Hilton Norfolk The Main

10/10 Excellent

"Clean and efficient"

Comfort Suites Airport

8/10 Good

"The bathroom wasn’t the cleanest, everything else was nice bed was very comfortable and location was great."

More cheap stays in Windsor

James River Inn & Suites

6045 Jefferson Ave Newport News VA

฿1,963

฿2,291 total

18 Oct - 19 Oct

includes taxes & fees

6.2/10 (222 reviews)

Key West Inn - Newport News

11845 Jefferson Ave Newport News VA

฿2,350

฿2,736 total

18 Oct - 19 Oct

includes taxes & fees

Sleep Inn & Suites Chesapeake - Portsmouth

3280 Western Branch Blvd Chesapeake VA

฿2,397

฿2,823 total

9 Nov - 10 Nov

includes taxes & fees

Comfort Suites Airport

12570 Jefferson Ave Newport News VA

฿3,110

฿3,610 total

3 Nov - 4 Nov

includes taxes & fees

8.8/10 Excellent! (1,162 reviews)

Quality Inn & Suites Olde Town

347 Effingham St Portsmouth VA

฿3,157

฿3,731 total

18 Oct - 19 Oct

includes taxes & fees

7.4/10 Good! (1,000 reviews)

stayAPT Suites Hampton

2122 Hartford Rd Hampton VA

฿3,994

฿4,661 total

15 Oct - 16 Oct

includes taxes & fees

Frequently asked questions

What's the best place to stay in Windsor?

Comfort Suites Airport, located 25.7 mi (41.4 km) from the heart of Windsor, is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Wyndham Garden Norfolk Downtown and Comfort Inn & Suites Hampton near Coliseum. See all available top hotels, or vacation rentals in Windsor.

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

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

What is staying in Windsor like?

Visitors to Windsor will definitely find plenty to explore and enjoy. There are 344 hotels and other accommodation options in the surrounding area. Find out more about Windsor.

What should I do while I'm visiting Windsor?

A couple of favourite places to visit are Lake Prince and Boykin's Tavern. You'll also find Windsor Castle Park and Chesapeake Square Mall in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.

What's the seasonal weather like in Windsor?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 7°C. Average annual precipitation for Windsor is 1327 mm.

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Find hotels in Windsor, VA from ฿2,034

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

1. Holiday Inn Express Hotel & Suites Suffolk by IHG

2. Hampton Inn Suffolk

3. Hilton Garden Inn Suffolk Riverfront

4. Hampton Inn Suites Smithfield

5. Home2 Suites By Hilton Suffolk

6. Brentwood Inn & Suites

7. Smithfield Station

8. Embassy Suites by Hilton Hampton Convention Center

9. Hyatt Place Hampton Convention Center

10. Courtyard by Marriott Suffolk Chesapeake

11. Holiday Inn Express & Suites Newport News by IHG

12. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

13. Red Roof Inn Suffolk

14. Comfort Suites Airport

15. Hampton Inn & Suites Chesapeake-Square Mall

16. Hilton Garden Inn Chesapeake/Suffolk

17. Hilton Norfolk The Main

18. Towneplace Suites By Marriott Newport News Airport

19. Norfolk Waterside Marriott

20. Candlewood Suites Chesapeake/Suffolk by IHG

Stay near popular Windsor attractions

Boykin's Tavern

Top Windsor Hotel Reviews

Embassy Suites by Hilton Hampton Convention Center

Sonesta Simply Suites Hampton

Sheraton Norfolk Waterside Hotel

Holiday Inn Express Hampton - Coliseum Central by IHG

Courtyard by Marriott Newport News Airport

Wyndham Garden Norfolk Downtown

Comfort Inn & Suites Hampton near Coliseum

Hilton Norfolk The Main

Comfort Suites Airport

More cheap stays in Windsor

James River Inn & Suites

Key West Inn - Newport News

Sleep Inn & Suites Chesapeake - Portsmouth

Comfort Suites Airport

Quality Inn & Suites Olde Town

stayAPT Suites Hampton

Frequently asked questions

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