Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

Shipside Suite Modern Fast WI-FI Cozy

Shipside Suite Modern Fast WI-FI Cozy
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"Very good communication with the host Area was quiet. Rental very clean & well stocked. Was a very enjoyable stay! "
United States
Rheta P.
The price is AU$452
includes taxes & fees
4 Mar - 5 Mar
Shipside Suite Modern Fast WI-FI Cozy

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$267
includes taxes & fees
22 Feb - 23 Feb
Private 1 Bed Apt - Historic Olde Towne Portsmouth

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is AU$383
includes taxes & fees
22 Feb - 23 Feb
The Speakeasy Downtown Newport News

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)
"The place was noce and quiet. "
United States
Tomar B.
The price is AU$413
includes taxes & fees
22 Feb - 23 Feb
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (36 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is AU$367
includes taxes & fees
21 Feb - 22 Feb
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (62 reviews)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is AU$192
includes taxes & fees
15 Mar - 16 Mar
stayAPT Suites Suffolk-Chesapeake

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
8.0 out of 10, Very good, (1 review)
"Host is communicative and relaxed (not trying to micromanage your stay). I forgot to check the pics and descriptions for a microwave but there isn’t one. Alternatively, there is a hot plate and a pot. I gave 4 out of 5 stars due to the coffeemaker not working and having one washcloth for two people but it was pleasant other than that. "
United States
Courtney R.
The price is AU$221
includes taxes & fees
21 Feb - 22 Feb
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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$388
includes taxes & fees
23 Feb - 24 Feb
Large 2 bedroom | Queen beds | Safe Area

❤️Ice Ice Baby❤️Downtown Newport News!

❤️Ice Ice Baby❤️Downtown Newport News!
Downtown Newport News
9.4 out of 10, Exceptional, (19 reviews)
"Was able to cook and relax for little getaway. "
United States
Rebecca S.
The price is AU$348
includes taxes & fees
22 Feb - 23 Feb
❤️Ice Ice Baby❤️Downtown Newport News!

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.8 out of 10, Exceptional, (17 reviews)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is AU$418
includes taxes & fees
23 Feb - 24 Feb
Comfortable & Private 2 Bedrm Cottage w/ King bed.

THE"HAVEN" (1 BEDROOM)

THE"HAVEN" (1 BEDROOM)
Franklin
9.6 out of 10, Exceptional, (7 reviews)
"Every time we stay it is very clean, well stocked, easy to enter and very quiet. "
United States
Neomia L.
The price is AU$316
includes taxes & fees
22 Feb - 23 Feb
THE"HAVEN" (1 BEDROOM)

Perfect for families!

Perfect for families!
Hudson Terrace
6.6 out of 10, (10 reviews)
"Great location for a family trip"
United States
Justin R.
The price is AU$445
includes taxes & fees
25 Feb - 26 Feb
Perfect for families!

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is AU$392
includes taxes & fees
22 Feb - 23 Feb
Ice Ice Baby Downtown Newport News

Spacious Downtown Apartment w/patio.

Spacious Downtown Apartment w/patio.
Downtown Norfolk
The price is AU$277
includes taxes & fees
18 Mar - 19 Mar
Spacious Downtown Apartment w/patio.

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Franklin
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful stay. This is a very cute and comfortable place. Will stay here again. "
United States
Denise P.
The price is AU$230
includes taxes & fees
21 Feb - 22 Feb
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)

❤️The Speakeasy❤️Downtown Newport News!

❤️The Speakeasy❤️Downtown Newport News!
Downtown Newport News
9.0 out of 10, Wonderful, (14 reviews)
"Clean and just as described, my 2nd time staying here, will definitely rent again."
United States
B H.
The price is AU$332
includes taxes & fees
22 Feb - 23 Feb
❤️The Speakeasy❤️Downtown Newport News!

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is AU$878
includes taxes & fees
28 Feb - 1 Mar
Centrally Located Hampton Roads Home w/ Game Room!

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$689
includes taxes & fees
22 Feb - 23 Feb
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
9.0 out of 10, Wonderful, (39 reviews)
"It was amazing. The house is dope, I highly recommend this house to anyone and I will be staying there again in the future!"
United States
Varstine S.
The price is AU$482
includes taxes & fees
23 Mar - 24 Mar
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Work Crew or Family-Friendly Lodging - 3 Bedrooms

Work Crew or Family-Friendly Lodging - 3 Bedrooms
Franklin
9.4 out of 10, Exceptional, (3 reviews)
"Nice quaint home, very comfortable. Had pictures and knick knacks around which made us feel right at home. Stayed here a week while exploring surrounding areas, the owners were quickly available with anything even though we did not have any problems needing addressed. Would definately stay here again if in the area."
United States
Mark C.
The price is AU$268
includes taxes & fees
22 Feb - 23 Feb
Work Crew or Family-Friendly Lodging - 3 Bedrooms
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$192 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?

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room : This holiday home rental outside of Windsor is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Carrollton Nike 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.