Top 10 Hotels in Windsor, VA in 2026 (from CNY394)

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Where to stay in Windsor?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Windsor on Hotels.com. These Windsor hotels consistently deliver on quality, location and traveler experience. Last updated on September 18, 2026.

Hypo-allergenic bedding available, in-room safe, desk, laptop workspace

1. Hampton Inn Suffolk

Suffolk

CNY798

CNY916 total

includes taxes & fees

Oct 6 - Oct 7

In-room safe, desk, iron/ironing board, cribs (free)

2. Hampton Inn Suites Smithfield

Smithfield

CNY654

CNY733 total

includes taxes & fees

Oct 11 - Oct 12

Suite, 1 Bedroom | Desk, iron/ironing board, cribs (surcharge), WiFi (free)

Desk, iron/ironing board, cribs (surcharge), WiFi (free)

3. Holiday Inn Express Hotel & Suites Suffolk by IHG

Suffolk

CNY684

CNY786 total

includes taxes & fees

Oct 19 - Oct 20

4. Hilton Garden Inn Suffolk Riverfront

Suffolk

CNY765

CNY878 total

includes taxes & fees

Oct 4 - Oct 5

5. Home2 Suites By Hilton Suffolk

Suffolk

CNY875

CNY1,004 total

includes taxes & fees

Sep 30 - Oct 1

6. Smithfield Station

Smithfield

CNY1,055

CNY1,218 total

includes taxes & fees

Sep 20 - Sep 21

7. Smithfield Inn

Smithfield

CNY1,401

CNY1,570 total

includes taxes & fees

Sep 23 - Sep 24

Combined shower/tub, free toiletries, towels

8. Brentwood Inn & Suites

Suffolk

CNY530

CNY611 total

includes taxes & fees

Oct 2 - Oct 3

In-room safe, desk, laptop workspace, blackout drapes

9. Comfort Suites Suffolk - Chesapeake

Suffolk

CNY607

CNY699 total

includes taxes & fees

Sep 27 - Sep 28

Desk, blackout drapes, iron/ironing board (on request), cribs (free)

10. Red Roof Inn Suffolk

Suffolk

CNY523

CNY620 total

includes taxes & fees

Oct 18 - Oct 19

11. Decoys

Suffolk

CNY1,285

CNY1,472 total

includes taxes & fees

Sep 20 - Sep 21

12. Courtyard by Marriott Suffolk Chesapeake

Suffolk

CNY624

CNY718 total

includes taxes & fees

Sep 23 - Sep 24

13. Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

CNY563

CNY661 total

includes taxes & fees

Oct 4 - Oct 5

14. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

CNY599

CNY703 total

includes taxes & fees

Oct 1 - Oct 2

Studio Suite, 1 King Bed with Sofa bed | Premium bedding, in-room safe, laptop workspace, blackout drapes

Premium bedding, in-room safe, laptop workspace, blackout drapes

15. Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

CNY547

CNY643 total

includes taxes & fees

Oct 19 - Oct 20

Standard Suite, 1 Queen Bed with Sofa bed, Non Smoking, Kitchen | 1 bedroom, premium bedding, desk, laptop workspace

Standard Suite, 1 Queen Bed with Sofa bed, Non Smoking, Kitchen | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

16. YourSpace Hotels Chesapeake

Western Branch North

CNY654

CNY765 total

includes taxes & fees

Sep 20 - Sep 21

Honeymoon Studio Suite, 1 King Bed, Non Smoking, Jetted Tub | Desk, laptop workspace, blackout drapes, iron/ironing board

17. Stonewood Inn & Suites Carrollton - Smithfield

Smithfield

CNY513

CNY569 total

includes taxes & fees

Sep 23 - Sep 24

18. Hilton Garden Inn Chesapeake/Suffolk

Suffolk

CNY616

CNY709 total

includes taxes & fees

Sep 27 - Sep 28

In-room safe, desk, iron/ironing board, WiFi (free)

19. Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

CNY505

CNY674 total

includes taxes & fees

Oct 19 - Oct 20

Standard Double Room, 2 Double Beds, Smoking | Bathroom | Combined shower/tub, towels

Standard Single Room, 1 King Bed, Non Smoking | Desk, WiFi (free), bed sheets

20. Bowers Hill Inn

Chesapeake

CNY426

CNY503 total

includes taxes & fees

Oct 2 - Oct 3

View all properties

Go beyond your typical stay in Windsor

Top landmarks in Windsor

Boykin's Tavern

8.0/10 (1 review)

If you're planning a bit of sightseeing during your trip, head to Boykin's Tavern— just one of the monuments in central Isle of Wight.

See properties

Check out reviews of Windsor hotels guests love

Hampton Inn Suffolk

Suffolk

10/10 Exceptional

Anonymous traveler

Holiday Inn Express Hotel & Suites Suffolk by IHG

Suffolk

10/10 Exceptional

Anonymous traveler

Hampton Inn Suites Smithfield

Smithfield

10/10 Exceptional

David

Hilton Garden Inn Suffolk Riverfront

Suffolk

10/10 Exceptional

Anonymous traveler

Decoys

Suffolk

10/10 Exceptional

Christina

YourSpace Hotels Chesapeake

Western Branch North

10/10 Exceptional

Valerie

Smithfield Inn

Smithfield

10/10 Exceptional

This is a very nice old historic inn. It has a restaurant that serves lunch and dinner, and a bar inside, as well as a shady garden with places to sit outside as you enjoy a drink or food. Nice big porch out front with chairs on it too. Our room had another sitting room in it that was nice to have. Not sure if they all do. It includes a free, great breakfast at a sister property a few doors down where the food is made fresh for your order. The property is well kept, clean, and the staff...

Douglas

Surry Seafood Company

Surry

10/10 Exceptional

I loved my stay! The views are spectacular and the food at the restaurant below is delicious. The staff there are lovely and very helpful. Be aware that there is no front desk, you just call to their sister property to get door codes for your room. I liked this but if you’re looking for a traditional hotel, this isn’t it. They were very helpful over the phone and let me have a later checkout. FYI, the restaurant does not serve breakfast, so be prepared to drive to Smithfield or Williamsburg...

Blair

Coffee/tea maker, full-size fridge, microwave, oven

1 bedroom, desk, laptop workspace, blackout drapes

stayAPT Suites Suffolk-Chesapeake

Suffolk

10/10 Exceptional

Devecia

stayAPT Suites Hampton

Coliseum Central

10/10 Exceptional

John

Courtyard by Marriott Suffolk Chesapeake

Suffolk

10/10 Exceptional

Malcolm

Hague Suite | Frette Italian sheets, premium bedding, down comforters, pillowtop beds

The Inn at Four Eleven York

West Freemason

10/10 Exceptional

Diana

Studio Suite, 1 Bedroom | Soundproofing, iron/ironing board

Towneplace Suites By Marriott Newport News Airport

Central Newport News

10/10 Exceptional

patricia

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

10/10 Exceptional

Deborah

Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

10/10 Exceptional

Anonymous traveler

Comfort Suites Airport

Central Newport News

10/10 Exceptional

Donna

Frequently Asked Questions

How much does a hotel room cost in Windsor?

You can choose a great hotel in Windsor from CNY394 with properties to suit all budgets and needs. If you're after an affordable hotel in Windsor that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Windsor hotels?

Discover great deals on Windsor hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. And make sure to check out our last-minute deals on Windsor hotels.

Can I book Windsor hotels with free cancellation?

In order to book a refundable Windsor hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

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