Title: Windsor, VA Cottage Rentals from $295 | Expedia.com

[Windsor Travel Guide](https://expedia.com/Windsor.dx3000460770)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d3000460770.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d3000460770.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d3000460770.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d3000460770.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d3000460770.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=3000460770&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=3000460770&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=3000460770&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=3000460770&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor cottages

![Property grounds](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/w1018h683x3y0-133e42a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/825456ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/ee6a7245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84048300/84048231/f95e63dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfortable & Private 2 Bedrm Cottage w/ King bed.

[](https://www.expedia.com/Portsmouth-Hotels-Comfortable-Private-2-Bedrm-Cottage-W-King-Bed.h84048231.Hotel-Information)

Portsmouth

9.8/10

Exceptional

(17 reviews)

"It was a great stay. Was there for work. Close for work and close to the beach. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Clayton M.

$254 nightly

$295 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Portsmouth-Hotels-Comfortable-Private-2-Bedrm-Cottage-W-King-Bed.h84048231.Hotel-Information)

![Cottage, 3 Bedrooms | Balcony](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/890dbbff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 3 Bedrooms | Living room | Smart TV](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/ecce39cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 3 Bedrooms | 3 bedrooms, free WiFi](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/ae3fe421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 3 Bedrooms | Beach | On the beach](https://images.trvl-media.com/lodging/79000000/78280000/78276200/78276199/b0f90467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Manor And Mutts #2 3 Bedroom Cottage by RedAwning

[](https://www.expedia.com/Norfolk-Hotels-Manor-And-Mutts-2-3-Bedroom-Cottage.h78276199.Hotel-Information)

Willoughby Spit

$514 nightly

$594 total

Feb 14 - Feb 15

Total with taxes and fees

[](https://www.expedia.com/Norfolk-Hotels-Manor-And-Mutts-2-3-Bedroom-Cottage.h78276199.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/93497329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/86d65edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/4ca87ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/124000000/123420000/123412000/123411909/adf90b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Centrally Located Hampton Roads Home w/ Game Room!

[](https://www.expedia.com/Portsmouth-Hotels-Centrally-Located-Hampton-Roads-Home-W-Game-Room.h123411909.Hotel-Information)

Portsmouth

$535 nightly

$618 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Portsmouth-Hotels-Centrally-Located-Hampton-Roads-Home-W-Game-Room.h123411909.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-25&endDate=2026-02-26&regionId=3000460770&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CABIN)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=COTTAGE)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Virginia%2C+United+States+of+America&regionId=3000460770&latLong=36.812424%2C-76.750946&adults=2&startDate=2026-05-12&d1=2026-05-12&endDate=2026-05-15&d2=2026-05-15&lodging=HOUSE_BOAT)

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## Top Windsor Hotel Reviews

![Comfort Inn & Suites Hampton near Coliseum](https://images.trvl-media.com/lodging/2000000/1550000/1545200/1545185/8b180fc8_y.jpg)

### Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent

"Friendly staff, clean rooms, quiet, and good breakfast "

[](https://expedia.com/Newport-News-Hotels-Country-Inn-Suites-By-Radisson.h1545185.Hotel-Information)

![Sonesta Simply Suites Hampton](https://images.trvl-media.com/lodging/1000000/70000/67800/67734/975448f7_y.jpg)

### Sonesta Simply Suites Hampton

10/10 Excellent

"Enjoyed my stay from the check-in to the cleanliness of the room to the check-out"

[](https://expedia.com/Newport-News-Hotels-Sonesta-Simply-Suites-Hampton.h67734.Hotel-Information)

![Sheraton Norfolk Waterside Hotel](https://images.trvl-media.com/lodging/1000000/20000/11700/11622/809a11a8_y.jpg)

### Sheraton Norfolk Waterside Hotel

10/10 Excellent

"The Staff were phenomenal, helped and courteous. Especially the front desk, and maids "

[](https://expedia.com/Norfolk-Hotels-Sheraton-Norfolk-Waterside-Hotel.h11622.Hotel-Information)

![Hyatt Place Hampton Convention Center](https://images.trvl-media.com/lodging/1000000/10000/7300/7213/89b7821f_y.jpg)

### Hyatt Place Hampton Convention Center

10/10 Excellent

"Clean and comfy "

[](https://expedia.com/Newport-News-Hotels-Hyatt-Place-Hampton-Convention-Center.h7213.Hotel-Information)

![Courtyard by Marriott Norfolk Downtown](https://images.trvl-media.com/lodging/1000000/890000/885900/885842/4fb817e1_y.jpg)

### Courtyard by Marriott Norfolk Downtown

10/10 Excellent

"Clean rooms, quick and easy check in/out. Valet parking is always a plus but it is expensive."

[](https://expedia.com/Norfolk-Hotels-Courtyard-By-Marriott-Norfolk-Downtown.h885842.Hotel-Information)

![Quality Inn & Suites Olde Town](https://images.trvl-media.com/lodging/1000000/160000/151500/151451/db57bf83_y.jpg)

### Quality Inn & Suites Olde Town

10/10 Excellent

"Clean rooms, fluffy beds, smells great, staff respectful and kind "

[](https://expedia.com/Portsmouth-Hotels-Quality-Inn-Suites-Olde-Town.h151451.Hotel-Information)

![Embassy Suites by Hilton Hampton Convention Center](https://images.trvl-media.com/lodging/2000000/1180000/1172300/1172219/5d92420f_y.jpg)

### Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent

"Everything was amazing. It was convenient to the venue for my concert. The morning breakfast was everything."

[](https://expedia.com/Newport-News-Hotels-Embassy-Suites-By-Hilton-Hampton-Convention-Center.h1172219.Hotel-Information)

![Comfort Suites Airport](https://images.trvl-media.com/lodging/2000000/1480000/1475200/1475139/b0999b75_y.jpg)

### Comfort Suites Airport

10/10 Excellent

"clean, large room! excellent breakfast selection; never say no to a waffle iron."

[](https://expedia.com/Newport-News-Hotels-Comfort-Suites-Airport.h1475139.Hotel-Information)

![Norfolk Waterside Marriott](https://images.trvl-media.com/lodging/1000000/20000/15000/14905/3501760d_y.jpg)

### Norfolk Waterside Marriott

10/10 Excellent

"Yes"

[](https://expedia.com/Norfolk-Hotels-Norfolk-Waterside-Marriott.h14905.Hotel-Information)

## Find out more about Windsor

## Windsor Cottages information

| Number of reviews | 16          |
| ----------------- | ----------- |
| Accommodation     | 57 Cottages |
| Lowest Price      | $295        |
| Highest Price     | $594        |

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- [Visit Isle of Wight ](https://www.expedia.com/Isle-Of-Wight.dx3000460059)
- [Isle of Wight Vacations ](https://www.expedia.com/Isle-Of-Wight.d3000460059.Destination-Travel-Guides)
- [Visit Carrsville ](https://www.expedia.com/Carrsville.dx3000355053)
- [Visit Ivor ](https://www.expedia.com/Ivor.dx3000355166)
- [Riddick's Folly House Museum ](https://www.expedia.com/Riddicks-Folly-House-Museum-Suffolk.d6301113.Vacation-Attraction)
- [Planters Peanut Center ](https://www.expedia.com/Planters-Peanut-Center-Suffolk.d6301076.Vacation-Attraction)
- [Suffolk Center for Cultural Arts ](https://www.expedia.com/Suffolk-Center-For-Cultural-Arts-Suffolk.d6301119.Vacation-Attraction)
- [Suffolk Seaboard Station Railroad Museum ](https://www.expedia.com/Suffolk-Seaboard-Station-Railroad-Museum-Suffolk.d6301125.Vacation-Attraction)
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- [Ivor Vacation Rentals ](https://www.expedia.com/Ivor-Vacation-Rentals.d3000355166.Travel-Guide-VacationRentals)
- [Suffolk Vacation Rentals ](https://www.expedia.com/Suffolk-Vacation-Rentals.d6981.Travel-Guide-VacationRentals)

- [Things to do in Suffolk ](https://www.expedia.com/Things-To-Do-In-Suffolk.d6981.Travel-Guide-Activities)