Windsor Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Windsor holiday rentals

Interior

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$905
HK$2,253 total
includes taxes & fees
23 Apr - 24 Apr
The Speakeasy Downtown Newport News
Interior

Charming Hampton Home w/ Yard: 2 Mi to Beach!

Charming Hampton Home w/ Yard: 2 Mi to Beach!
3.0 star property
Hampton
Charming Hampton Home w/ Yard: 2 Mi to Beach!
Property grounds

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is HK$940
HK$2,113 total
includes taxes & fees
23 Apr - 24 Apr
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Dining

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is HK$627
HK$2,060 total
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Fridge, microwave, oven, stovetop

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is HK$783
HK$2,257 total
includes taxes & fees
23 Apr - 24 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (19 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is HK$775
HK$2,473 total
includes taxes & fees
26 Apr - 27 Apr
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Dining

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is HK$759
HK$3,008 total
includes taxes & fees
26 Apr - 27 Apr
Sojourn | Coastal Cottage | 3 BR
Fridge, microwave, oven, stovetop

4 Bedroom Cottage - 5 Minutes from both beaches

4 Bedroom Cottage - 5 Minutes from both beaches
Hampton
9.4 out of 10, Exceptional, (29 reviews)
"Clean house. Very easy check in and out process. "
United States
Ryan P.
The price is HK$1,706
HK$4,210 total
includes taxes & fees
27 Apr - 28 Apr
4 Bedroom Cottage - 5 Minutes from both beaches
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (70 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is HK$932
HK$1,070 total
includes taxes & fees
4 May - 5 May
stayAPT Suites Suffolk-Chesapeake
Exterior

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is HK$2,093
HK$4,251 total
includes taxes & fees
26 Apr - 27 Apr
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
2 bedrooms

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is HK$859
HK$2,193 total
includes taxes & fees
23 Apr - 24 Apr
Ice Ice Baby Downtown Newport News
Interior

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is HK$2,060
HK$4,843 total
includes taxes & fees
30 Apr - 1 May
Centrally Located Hampton Roads Home w/ Game Room!
Interior

Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is HK$1,434
HK$2,821 total
includes taxes & fees
19 May - 20 May
Large 2 bedroom | Queen beds | Safe Area
Dining

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is HK$1,938
HK$4,567 total
includes taxes & fees
27 Apr - 28 Apr
Wooded Wonderland
Property grounds

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is HK$634
HK$1,455 total
includes taxes & fees
27 Apr - 28 Apr
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Marina

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is HK$1,566
HK$2,563 total
includes taxes & fees
25 Apr - 26 Apr
Your Tropical Oasis awaits in Hampton Roads Virginia
Interior

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
North Newport News
10.0 out of 10, Exceptional, (21 reviews)
"Was a great place for families with adults and children. (12,10,8). 10 min or so to Busch Gardens. "
United States
Dwayne R.
The price is HK$4,793
HK$7,130 total
includes taxes & fees
10 May - 11 May
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard
Property grounds

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Willoughby Spit
7.8 out of 10, Good, (12 reviews)
"Loved the view and communication with owner was exceptional. "
United States
Dottie H.
The price is HK$2,107
HK$4,068 total
includes taxes & fees
26 Apr - 27 Apr
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Smart TV

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"It’s was great staying "
United States
Shalena K.
The price is HK$783
HK$1,464 total
includes taxes & fees
3 May - 4 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Interior

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis

5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
Hampton
9.8 out of 10, Exceptional, (38 reviews)
"Everyone loved the place!"
United States
Gail R.
The price is HK$4,135
HK$6,193 total
includes taxes & fees
23 Apr - 24 Apr
5 Minutes to Boo Williams Sportsplex! Family-Fun Grotto Waterfall Bethel Oasis
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.
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Top Windsor Hotel Reviews

YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

10/10 Excellent
"Friendly staff. Fully stocked kitchen. Clean property. Good security "
Danielle 4-night trip
Posted 8 hours ago
YourSpace Hotels Chesapeake

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Historic Old Towne Southern Charm: This holiday home rental outside of Windsor offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Windsor?

Cultural attractions include Boykin's Tavern, whereas Lake Prince is a spot to enjoy nature. In the wider area, you’ll find Planters Peanut Center and Windsor Castle Park.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.