Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is AU$401
includes taxes & fees
23 Apr - 24 Apr
The Speakeasy Downtown Newport News

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

Charming Hampton Home w/ Yard: 2 Mi to Beach!
3.0 star property
Hampton
The price is AU$553
includes taxes & fees
22 Apr - 23 Apr
Charming Hampton Home w/ Yard: 2 Mi to Beach!

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 AU$378
includes taxes & fees
22 Apr - 23 Apr
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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 AU$368
includes taxes & fees
25 Apr - 26 Apr
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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 AU$405
includes taxes & fees
23 Apr - 24 Apr
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (18 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is AU$439
includes taxes & fees
22 Apr - 23 Apr
Comfortable & Private 2 Bedrm Cottage w/ King bed.

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 AU$535
includes taxes & fees
28 Apr - 29 Apr
Sojourn | Coastal Cottage | 3 BR

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 AU$773
includes taxes & fees
26 Apr - 27 Apr
4 Bedroom Cottage - 5 Minutes from both beaches

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 AU$185
includes taxes & fees
4 May - 5 May
stayAPT Suites Suffolk-Chesapeake

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 AU$761
includes taxes & fees
26 Apr - 27 Apr
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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
Ice Ice Baby Downtown Newport News

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
Centrally Located Hampton Roads Home w/ Game Room!

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 AU$499
includes taxes & fees
19 May - 20 May
Large 2 bedroom | Queen beds | Safe Area

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 AU$818
includes taxes & fees
27 Apr - 28 Apr
Wooded Wonderland

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 AU$262
includes taxes & fees
28 Apr - 29 Apr
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is AU$457
includes taxes & fees
24 Apr - 25 Apr
Your Tropical Oasis awaits in Hampton Roads Virginia

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 AU$1,231
includes taxes & fees
10 May - 11 May
8 miles to Bush Gardens/5 Bedroom Rancher with 2 master's/ playground/backyard

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 AU$715
includes taxes & fees
26 Apr - 27 Apr
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

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 AU$263
includes taxes & fees
3 May - 4 May
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 AU$1,101
includes taxes & fees
28 Apr - 29 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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$185 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.