Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (40)
"Nice cozy place to go with your family "
The price is €118
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Suffolk-Chesapeake

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

7.6 out of 10, Good, (8)
"Wonderful property!! My family and I had a great time. The location is very convenient to about everything. "
The price is €497
includes taxes & fees
1 Sept - 2 Sept
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

9.8 out of 10, Exceptional, (138)
"Great location very clean and cozy room. Beautiful area!!"
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!

Cozy Suite at the Beach

8.4 out of 10, Very good, (61)
"It was alright "
Cozy Suite at the Beach

Boat House Studio - Water Front Pets WiFi Smart TV by RedAwning

2.0 out of 10, (1)
"The pictures are inaccurate.A family was staying right at the deck.The grilling area is in rough shape.I will purchase canceling insurance for now on because of this property.Very outdated.Needs some money put into it.It has good potential but a no thankyou for me.Parking was terrible for me as I had a big work truck.And outdated appliances.Live and learn."
Boat House Studio - Water Front Pets WiFi Smart TV by RedAwning

Beachfront House on James River. Near Historic Jamestowne and Williamsburg

10.0 out of 10, Exceptional, (197)
"Great place and location "
Beachfront House on James River. Near Historic Jamestowne and Williamsburg

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (63)
"Magnificent view, accommodation s and amenities. Highly Recommended "
The price is €307
includes taxes & fees
2 Sept - 3 Sept
Luxury Riverfront Condo w/ sunrise & sunset views

Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

9.0 out of 10, Wonderful, (32)
"We had a great time. The house needs a little cosmetic things done to the outside but the inside was beautiful. It is right on the beach and our kids loved going out to play in the sand."
Manor and Mutts #2 - Beach Front, Pet Friendly, High Speed WiFi

Perfect for families!

6.6 out of 10, (8)
"we enjoy the stay and we’ll book again great location located right behind the Newport police station. There’s also lots of things to do in the location. A big pond for fishing my family enjoyed."
The price is €256
includes taxes & fees
2 Sept - 3 Sept
Perfect for families!

3 BEDROOM 2 BATH ON THE WATER

9.4 out of 10, Exceptional, (72)
"Easy access as family is close by should’ve brought our boat nice newer dock clean & neat facilities everything worked would stay here again being priced right"
3 BEDROOM 2 BATH ON THE WATER

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

9.0 out of 10, Wonderful, (16)
"House was clean and welcoming. Communication was great. I would stay again in a heart beat. I’m active duty military and host was very accommodating. "
The price is €212
includes taxes & fees
15 Sept - 16 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Riverfront Fun: Quiet Home Near Hampton Coastline

3.0 star property
Riverfront Fun: Quiet Home Near Hampton Coastline

Beachhouse

2.6 out of 10, (4)
"I made two bookings, very easy but one canceled abruptly and the second turned out to be a non-available property and I did not find out until an before check-in. I was credited 100 for my trouble. I recommend that anyone that chooses this method, to reach out to the management agency or owner immediately to get the actual status of the property."
Beachhouse

Ice Ice Baby Downtown Newport News

2.0 star property
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
Ice Ice Baby Downtown Newport News

WaterFront Ground Floor - 1 BR, WiFi Smart, TV, Pet Friendly

6.0 out of 10, (1)
"Pictures were accurate for the "apartment" that was listed as a stand alone house. Playground for dogs was not fenced in by gates. Water access and pier listed was non existent. Pier/deck over water was once standing however, now all the boards are on the shoreline/beach area. Loose boards with nails piled on shoreline. Parking is TIGHT and only 4 very tight spots for vehciles. 1 parking spot is used by owner who lives upstairs of the apartments. I have pictures if needed."
WaterFront Ground Floor - 1 BR, WiFi Smart, TV, Pet Friendly

Heart of City - Pool - Parking - Self check-in

2.0 out of 10, (1)
"Property manager canceled my stay with no notice. I had already driven a great distance to be there. Took several days for them to issue the refund despite the fact that they canceled the reservation same day. Actually they told me I had to cancel the reservation on my end. I assume this was so they would still get the money from the reservation, but I called to cancel it and explain the situation. Long story short don’t book here."
The price is €237
includes taxes & fees
22 Sept - 23 Sept
Heart of City - Pool - Parking - Self check-in

Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

8.8 out of 10, Excellent, (48)
"Had an overall nice stay. Very clean. Great location was able to take a walk on the beach and that was definitely needed. Was in town due to family emergency and booked quickly. In the pictures there are 3 beds in room but there were only 2 when we got there a full size and twin. So my daughters were mad they had to sleep together but they got over it. Living room was cold and bedroom got hot.We also booked for 5 people but there were only 3 towels and 3 wash cloths. But made the best of it and...
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi

Large 2 bedroom | Queen beds | Safe Area

7.8 out of 10, Good, (8)
"House looks like the pictures which makes that a hugh plus. Property waa very well maintained. "
The price is €257
includes taxes & fees
1 Sept - 2 Sept
Large 2 bedroom | Queen beds | Safe Area

The Boat House on the Bay - On the water; Pet Friendly; WiFi

7.8 out of 10, Good, (21)
"Another fun vacation in the books."
The Boat House on the Bay - On the water; Pet Friendly; WiFi

Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area

9.8 out of 10, Exceptional, (68)
"The cottage is obviously well cared for. Its location is great - right next to the river ferry - and the small beach is a great place to relax. Homeowner was very attentive to every need."
Waterfront Cottage With Private Beach & Pier - James River - Williamsburg Area
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

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, apart-hotels, 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 favorite 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 depends 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 €118 per night. Entering your travel dates in the search wizard you might find 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?

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!: This holiday home rental outside of Windsor has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Windsor Castle Park and Chesapeake Square Mall.

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.