Windsor Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Windsor

stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (28)
"Great place to stay!"
The price is HK$934
HK$1,073 total
includes taxes & fees
4 Aug - 5 Aug
stayAPT Suites Suffolk-Chesapeake
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Terrace/patio

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

7.0 out of 10, Good, (6)
The price is HK$3,132
HK$5,440 total
includes taxes & fees
14 Jul - 15 Jul
Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!
Beachhouse
Marina

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

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

9.0 out of 10, Wonderful, (30)
"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
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

9.0 out of 10, Wonderful, (96)
"It's a cute house, just steps away from the beach. We had a great time enjoying all the sights around town and beach during our trip. They had everything we needed to enjoy our stay...Our host was awesome and communicated with me about everything "
Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach
Boat House Studio - Water Front Pets WiFi Smart TV by RedAwning
Property grounds

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
Mariners Cove Waterfront with Private Dock
Interior

Mariners Cove Waterfront with Private Dock

7.4 out of 10, Good, (32)
"If you’re looking for a quiet location to spend your weekend at the beac"
Mariners Cove Waterfront with Private Dock
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning
Property grounds

Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning

7.6 out of 10, Good, (9)
"We needed a reasonably priced home that was located near points of interest and easy to get to. The home was very roomy, a large kitchen, comfortable dining area with plenty of seating for all, large TV in the living room with plenty of comfortable seats. Three full bathrooms enough for all. "
Water Front Oasis (4-Bedroom Home) - Pets Allowed by RedAwning
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (12)
"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 HK$785
HK$1,694 total
includes taxes & fees
17 Jul - 18 Jul
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Harbor Delight on the Bay - All the modern amenities plus a Private Sandy Beach!
On the beach, sun-loungers

Harbor Delight on the Bay - All the modern amenities plus a Private Sandy Beach!

8.6 out of 10, Excellent, (27)
"There’s plenty of room for friends and family. Great way to entertain guess from out of town. Perched on a very quite and convenient location. Excellent parking for up to four cars."
Harbor Delight on the Bay - All the modern amenities plus a Private Sandy Beach!
Heart of City - Pool - Parking - Self check-in
Terrace/patio

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 HK$997
HK$2,183 total
includes taxes & fees
14 Jul - 15 Jul
Heart of City - Pool - Parking - Self check-in
Cozy Suite - Pet friendly, Beach Side by RedAwning
Beach nearby

Cozy Suite - Pet friendly, Beach Side by RedAwning

9.4 out of 10, Exceptional, (6)
"Nice location and host was very helpful.."
Cozy Suite - Pet friendly, Beach Side by RedAwning
Delightful 1 Bedroom RV Near Ft. Eustis
Smart TV, video games

Delightful 1 Bedroom RV Near Ft. Eustis

9.0 out of 10, Wonderful, (2)
"We hadn’t stayed in an RV before, so this was a unique experience for us. Very clean & cozy accommodations and located close to many tourist attractions in the surrounding area. Easy parking out front was helpful, and the detailed & friendly communication with the host was also appreciated."
Delightful 1 Bedroom RV Near Ft. Eustis
3 BEDROOM 2 BATH ON THE WATER
Outdoor dining

3 BEDROOM 2 BATH ON THE WATER

9.4 out of 10, Exceptional, (69)
"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
The Boat House on the Bay - On the water; Pet Friendly; WiFi
Terrace/patio

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

7.8 out of 10, Good, (20)
"Another fun vacation in the books."
The Boat House on the Bay - On the water; Pet Friendly; WiFi
Cozy Bay View - BeachSide, Pet Friendly, Wi-Fi
On the beach

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

8.8 out of 10, Excellent, (46)
"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
Luxury Riverfront Condo w/ sunrise & sunset views
Marina

Luxury Riverfront Condo w/ sunrise & sunset views

9.6 out of 10, Exceptional, (60)
"Our stay was amazing. The condo was immaculate, the kitchen was well stocked and the Riverview was outstanding. "
The price is HK$1,406
HK$2,821 total
includes taxes & fees
14 Jul - 15 Jul
Luxury Riverfront Condo w/ sunrise & sunset views
GREAT HOUSE ON LITTLE BAY WITH PIER
Outdoor dining

GREAT HOUSE ON LITTLE BAY WITH PIER

9.8 out of 10, Exceptional, (98)
"Nice neighborhood, beautiful house. Very nice to fish off the dock."
GREAT HOUSE ON LITTLE BAY WITH PIER
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino
Microwave, coffee/tea maker, cookware/dishes/utensils, dining tables

Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino

9.6 out of 10, Exceptional, (9)
"Place was clean, check-in was easy and the backyard was great!"
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino
Water Front Delight on the Bay
Terrace/patio

Water Front Delight on the Bay

8.0 out of 10, Very good, (23)
"It was a quiet and peaceful experience. My family enjoyed it immensely. "
Water Front Delight on the Bay
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 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.