Windsor Holiday Rentals, Virginia: Private House Rentals

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Our top choices for Windsor hotels

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

A gym with exercise equipment, a red exercise ball, and a motivational sign.

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

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

1. Hampton Inn Suffolk

Suffolk

Tracy

฿3,774

฿4,335 total

includes taxes & fees

14 Sept - 15 Sept

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

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.

A Holiday Inn Express & Suites building with a brick facade, a covered entrance, and a green roof.

A swimming pool with lounge chairs and a building with a red brick facade.

2. Holiday Inn Express Hotel & Suites Suffolk by IHG

Suffolk

Tanya

฿3,642

฿4,185 total

includes taxes & fees

13 Sept - 14 Sept

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

A snack and sundries section with shelves stocked with various treats and a wall mural depicting food items.

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

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.

3. Hampton Inn Suites Smithfield

Smithfield

Kimric

฿3,502

฿3,923 total

includes taxes & fees

13 Sept - 14 Sept

A Red Roof Inn reception area with two leather chairs, a wall-mounted sign, and a view of the outside.

A reception area with a counter, an ATM, a door labeled "Office," and a window with a view.

A coffee station with a coffee machine, cups, and a poster advertising RediRewards.

4. Red Roof Inn Suffolk

Suffolk

Saddie

฿2,833

฿3,346 total

includes taxes & fees

31 Aug - 1 Sept

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

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

A spacious hotel lobby with a red carpet, large chandeliers, and seating areas.

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

5. Hilton Garden Inn Suffolk Riverfront

Suffolk

Eric

฿3,774

฿4,335 total

includes taxes & fees

20 Sept - 21 Sept

A Comfort Suites hotel with a large parking lot, multiple floors, and a well-lit entrance.

A hotel dining area with multiple tables and chairs, a kitchen area, and large windows offering views.

A hotel room with a blue sofa, a bed with a red blanket, a desk, and a lamp. There are three framed pictures on the wall.

A reception area with a curved counter, a seating area with a blue sofa and red chairs, and a glass door entrance.

6. Comfort Suites Suffolk - Chesapeake

Suffolk

Nicholas

฿3,056

฿3,517 total

includes taxes & fees

6 Sept - 7 Sept

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

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

A modern lounge area with a round table, two green armchairs, a beige sofa, and large windows with sheer curtains.

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

7. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

Allen

฿2,959

฿3,470 total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with two beds, a nightstand, a desk, a sink, and a door leading to another room.

A bathroom with a bathtub, a shower curtain, and beige tiled walls.

A multi-story building with a parking lot in front.

A hotel room with a bed, a desk with a chair, a television, a minibar, and a door leading to a balcony.

8. COUNTRY HOST INN

Franklin

Deborah

฿1,788

฿1,985 total

includes taxes & fees

31 Aug - 1 Sept

A modern kitchen with a long countertop, wooden cabinets, and a dining area with chairs.

A hotel room with a large bed, a desk with a lamp, and a view of a green outdoor area.

A living room with a blue sofa, orange armchairs, a coffee table, and a patterned rug.

A reception area with a counter, seating, a television, and a clock on the wall.

9. Quality Inn & Suites Suffolk West

Suffolk

"While I was still in the room, the housekeeper came in asking for tips! It made me really uncomfortable, almost like when you’re in Jamaica and they try and force you to buy their stuff!! I literally had to tell her to get out of my room and she said I come back in 10 minutes and you give me tips! Not sure why I would tip her anyway because it was run down and dirty, but the choices in that area are limited and I had to sleep. I didn’t not try the free breakfast and the pool was closed."

Susan

฿3,581

฿4,115 total

includes taxes & fees

24 Sept - 25 Sept

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.

10. Smithfield Station

Smithfield

James

฿5,212

฿6,013 total

includes taxes & fees

31 Aug - 1 Sept

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

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

A bedroom with a bed, a desk with a TV, and a door leading outside.

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

11. Brentwood Inn & Suites

Suffolk

Gary

฿2,871

฿3,306 total

includes taxes & fees

31 Aug - 1 Sept

A spacious lobby with a reception desk, green seating, and a large TV screen.

A Holiday Inn Express & Suites building with a covered entrance and a brick facade.

An indoor swimming pool with clear water, a reception desk, and a few lounge chairs.

A hotel room with a large bed, bedside tables, a desk, a chair, a TV, and a window.

12. Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

Brian

฿3,079

฿3,607 total

includes taxes & fees

13 Sept - 14 Sept

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

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

13. Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

Yvonne

฿2,688

฿3,157 total

includes taxes & fees

7 Sept - 8 Sept

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.

14. Courtyard by Marriott Suffolk Chesapeake

Suffolk

Keisha

฿3,311

฿3,808 total

includes taxes & fees

7 Sept - 8 Sept

A hotel lobby with a fireplace, seating area, and a television on the wall.

A hotel room with a large bed, bedside tables with lamps, a chair, and a framed picture on the wall.

A lobby with a fireplace, seating area, and a staircase.

A swimming pool with a tiled deck, a changing room, and a seating area with chairs and tables.

15. Hilton Garden Inn Chesapeake/Suffolk

Suffolk

Shana

฿3,774

฿4,335 total

includes taxes & fees

6 Sept - 7 Sept

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.

16. Home2 Suites By Hilton Suffolk

Suffolk

฿4,208

฿4,831 total

includes taxes & fees

30 Sept - 1 Oct

A hotel room with a bed, a red sofa, a wooden table, a desk with a chair, and a window with curtains.

A spacious indoor dining area with multiple tables and booths, large windows, and a fireplace.

An indoor swimming pool with dolphin murals, a sunroof, and seating areas.

17. Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

Nwanneka

฿2,482

฿3,318 total

includes taxes & fees

9 Sept - 10 Sept

A modern living room with a sofa, a dining table, and a kitchen in the background.

A hotel room with a bed, a desk, a TV, and a painting of a pier.

A modern hotel lobby with a reception desk, a dining area, and a flat-screen TV mounted on the wall.

A modern kitchen with a built-in microwave, coffee maker, and refrigerator. There is a dining area with a table and chairs, and a staircase leading to an upper level.

18. Super 8 by Wyndham Franklin

Franklin

Stan

฿2,881

฿3,284 total

includes taxes & fees

27 Sept - 28 Sept

A two-story motel with a brick facade and a red roof.

A bathroom with a bathtub, a shower curtain, and a towel rack.

A hotel room with a large bed, a headboard with lights, a telephone, and a painting on the wall.

A parking lot with two trucks and a grassy area with trees in the background.

19. American Inn Chesapeake – Portsmouth

Chesapeake

WILLIAM

฿2,246

฿2,649 total

includes taxes & fees

31 Aug - 1 Sept

A hotel room with two beds, a desk with a TV, a mirror, and a bathroom visible through an open door.

A bathroom with a bathtub, toilet, and shower curtain.

A hotel room with a bed, bedside tables, a telephone, and a wall-mounted light fixture.

A bathroom with a toilet, bathtub, shower curtain, and towel rack.

20. Bowers Hill Inn

Chesapeake

Sean

฿2,102

฿2,483 total

includes taxes & fees

1 Sept - 2 Sept

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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

Comfort Suites Airport

10/10 Excellent

"The front desk staff is always great in the afternoon when we check in!"

Hyatt Place Hampton Convention Center

10/10 Excellent

"Room was very clean and breakfast was good."

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent

"Great staff and a great breakfast"

Kingsmill Resort

10/10 Excellent

"Food was just okay."

The Landing at Hampton Marina, Tapestry Collection by Hilton

10/10 Excellent

"Clean room Food was great"

YourSpace Hotels Chesapeake

8/10 Good

"Overall, we really enjoyed our stay at this hotel. The amenities were excellent, and the customer service was great from check-in through check-out. The hotel was very clean, organized, and well maintained overall. There were a few minor maintenance details that could have been improved, but nothing that negatively affected our stay. We did have an issue with the elevator card reader, but the maintenance staff responded quickly and resolved it right away, which we really appreciated. Overall, we had a very positive experience and would definitely consider staying here again."

Wyndham Garden Norfolk Downtown

8/10 Good

"The front desk was awesome! The room was okay, clean but old, maintenence had to come put the bathroom door back on, its a sliding door that came off..they also had to come in to check the bathroom wall which the tile was pushed in. We couldn't really use the tub since the water only came from the shower head. We were there 4 nights and I had to steal toilet paper off the housekeeping cart because they never came in our room, luckily we had extra towels to start with. There was a door attached to the next room with locks on both sides, but a housekeeper was in there on her phone and I literally heard her whole conversation through the walls/doors..We thought there was free continental breakfast but turns out you have to pay..its a bit pricey too but the girl working was great and could seriously make some food, the omelets were spectacular! It's an old building and it definitely shows, but the girls at the desk are great and the omelets made it a good trip."

Country Inn & Suites by Radisson, Hampton Coliseum

10/10 Excellent

"Comfortable stay"

Holiday Inn Newport News - Hampton by IHG

8/10 Good

"Stay was great for a solo traveler , clean was the most important thing and it was , room good size , free parking was great, staff was nice"

More cheap stays in Windsor

James River Inn & Suites

6045 Jefferson Ave Newport News VA

฿1,937

฿2,260 total

7 Sept - 8 Sept

includes taxes & fees

Budget Lodge

3244 Western Branch Blvd Chesapeake VA

฿2,102

฿2,583 total

31 Aug - 1 Sept

includes taxes & fees

Key West Inn - Newport News

11845 Jefferson Ave Newport News VA

฿2,649

฿3,079 total

1 Sept - 2 Sept

includes taxes & fees

6.4/10 (452 reviews)

Comfort Inn Newport News - Hampton I-64

12330 Jefferson Ave Newport News VA

฿3,003

฿3,486 total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Quality Inn & Suites Olde Town

347 Effingham St Portsmouth VA

฿3,114

฿3,681 total

1 Sept - 2 Sept

includes taxes & fees

7.4/10 Good! (1,002 reviews)

Comfort Suites Airport

12570 Jefferson Ave Newport News VA

฿3,237

฿3,755 total

20 Sept - 21 Sept

includes taxes & fees

8.8/10 Excellent! (1,117 reviews)

Frequently asked questions

What's the best place to stay in Windsor?

Wyndham Garden Norfolk Downtown, located 25.8 mi (41.6 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 Comfort Suites Airport and Kingsmill Resort. 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 Planters Peanut Center 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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Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, VA from ฿2,260

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. Hampton Inn Suffolk

2. Holiday Inn Express Hotel & Suites Suffolk by IHG

3. Hampton Inn Suites Smithfield

4. Red Roof Inn Suffolk

5. Hilton Garden Inn Suffolk Riverfront

6. Comfort Suites Suffolk - Chesapeake

7. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

8. COUNTRY HOST INN

9. Quality Inn & Suites Suffolk West

10. Smithfield Station

11. Brentwood Inn & Suites

12. Holiday Inn Express Hotel & Suites Chesapeake by IHG

13. Hampton Inn & Suites Chesapeake-Square Mall

14. Courtyard by Marriott Suffolk Chesapeake

15. Hilton Garden Inn Chesapeake/Suffolk

16. Home2 Suites By Hilton Suffolk

17. Comfort Inn & Suites Chesapeake - Portsmouth

18. Super 8 by Wyndham Franklin

19. American Inn Chesapeake – Portsmouth

20. Bowers Hill Inn

Stay near popular Windsor attractions

Boykin's Tavern

Top Windsor Hotel Reviews

Comfort Suites Airport

Hyatt Place Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

Kingsmill Resort

The Landing at Hampton Marina, Tapestry Collection by Hilton

YourSpace Hotels Chesapeake

Wyndham Garden Norfolk Downtown

Country Inn & Suites by Radisson, Hampton Coliseum

Holiday Inn Newport News - Hampton by IHG

More cheap stays in Windsor

James River Inn & Suites

Budget Lodge

Key West Inn - Newport News

Comfort Inn Newport News - Hampton I-64

Quality Inn & Suites Olde Town

Comfort Suites Airport

Frequently asked questions

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