Windsor Holiday Rentals

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Holiday Rentals in Windsor

Welcome to Carrollton
10.0 out of 10, Exceptional, (6)
"This property was perfect for everything that you would want in a family vacation. We had 11 family members in the house and there was plenty of room. The main area was great for a breakfast we hosted for 18 people. The grounds were large with a playground for the children and outdoor seating for all. We could not ask for more."
Welcome to Carrollton
Guesthouse in ideal location with private entrance
10.0 out of 10, Exceptional, (1)
"Nearby outdoor track. Friendly neighbors. Very nice"
The price is NZ$357
per night
24 Jun - 25 Jun
Guesthouse in ideal location with private entrance
HOME AWAY FROM HOME
9.4 out of 10, Exceptional, (3)
"Communicate with properly manager whats A1"
HOME AWAY FROM HOME
Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.
10.0 out of 10, Exceptional, (18)
"Booked this house to attend a Morgan Wallen concert at Virginia Beach. Got stuck in traffic and was running extremely behind. When we arrived at the house, to our surprise there were snacks and cold water in the frig, this was great since we had no time to grab dinner before the concert. This was probably one of the best stocked houses that I have ever stayed in. The house was well decorated and was super clean. The neighborhood was quiet and we definitely felt safe. The pool was great and beach...
Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.
The Vine--4 Bedrooms
10.0 out of 10, Exceptional, (7)
"The house is very clean and well equipped.There were many special touches."
The Vine--4 Bedrooms
Private apartment close to all major Hampton Roads attractions.
10.0 out of 10, Exceptional, (1)
"The place was super clean. Very nice. It was me, my brother and Sparky the dog. It's a very nice neighborhood. A little too much traffic for long dog walks but there are plenty of great parks nearby. There's a very cute store right next door. It was centrally located to every where we wanted to be. Again, very good neighborhood and amazingly clean and bright space."
Private apartment close to all major Hampton Roads attractions.
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
10.0 out of 10, Exceptional, (22)
"Wonderful stay."
The price is NZ$283
per night
19 Jun - 20 Jun
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Bright Chesapeake Home Near Shopping & Dining
10.0 out of 10, Exceptional, (2)
"Worked great our for weekend baseball trip"
Bright Chesapeake Home Near Shopping & Dining
Luxury Home close to Rivers Casino and Va Beach!
Luxury Home close to Rivers Casino and Va Beach!
Spacious Chesapeake Home w/ Pool Table!
8.0 out of 10, Very good, (3)
"The house was very nice and the property manager was very nice and very helpful and quick to respond. Very nice & quiet neighborhood. FYI: All the rooms are up stairs except there is a daybed and a pull out couch down stairs (but they are pretty comfortable)."
Spacious Chesapeake Home w/ Pool Table!
Experience Chesapeake Your Way and Relax with Golf Entire home
10.0 out of 10, Exceptional, (4)
"We enjoyed it it a lot! 1 minor situation but the owner was all over it and made it right immediately. He even called to check on us and make sure it was handled. I would definitely stay again and recommend it to a friend."
The price is NZ$512
per night
24 Jun - 25 Jun
Experience Chesapeake Your Way and Relax with Golf Entire home
Private Guest Suite in Historic house
The price is NZ$271
per night
30 Jun - 1 Jul
Private Guest Suite in Historic house
Cavalier Manor: Pool, Luxury Home, & Scenic Views
10.0 out of 10, Exceptional, (2)
"I had a small wedding at this property, and let me tell you that it was the wedding of my dreams. From the beautiful interior to the extravagant exterior, my guest was amazed at the beauty of this home. We also stayed a total of five days and the property manager checked on us regularly to make sure we had a comfortable stay. I cannot express how thoughtful and beautiful this home is. I wish I could stay forever. I highly recommend this property."
Cavalier Manor: Pool, Luxury Home, & Scenic Views
Peace on the Brewers River.
10.0 out of 10, Exceptional, (43)
"The hosts were attentive. The home was beautiful and well kept. The views of the water and wildlife were amazing. This getaway was all that we could have hoped for. We would definitely stay here again."
Peace on the Brewers River.
Charming Smithfield House: Walk to Downtown!
10.0 out of 10, Exceptional, (1)
"We used this home for some out of town guests to stay while they were visiting."
Charming Smithfield House: Walk to Downtown!
The Mermaids Lair 🧜‍♀️
8.0 out of 10, Very good, (4)
"Nice waterfront spot, bed was comfy"
The Mermaids Lair 🧜‍♀️
Bright Chesapeake Home Near Shopping & Dining
3.0 star property
Bright Chesapeake Home Near Shopping & Dining
THE"HAVEN" (1 BEDROOM)
10.0 out of 10, Exceptional, (1)
"Very nice place to stay and close to the venue for my son's wedding. bed was comfortable."
The price is NZ$384
per night
19 Jun - 20 Jun
THE"HAVEN" (1 BEDROOM)
The "KINGSDALE" 2 Bedrooms
10.0 out of 10, Exceptional, (3)
"This property is pictured and described accurately. They provide you everything needed to have a safe and cozy stay. Communication is effortless and the owner is very responsive! I’d recommend anyone looking to come to Franklin, VA on business to stay here and enjoy a good night rest."
The price is NZ$489
per night
19 Jun - 20 Jun
The "KINGSDALE" 2 Bedrooms
Family-Friendly Lodging - 3 Bedrooms
Family-Friendly Lodging - 3 Bedrooms
Don't see what you're looking for?
See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

Comfort Suites Suffolk - Chesapeake
2.5 star property
7.8 out of 10, Good, (1014)
"Love this hotel comfortable room great breakfast will come again"
The price is NZ$209
per night
26 Jun - 27 Jun
Comfort Suites Suffolk - Chesapeake
Sleep Inn & Suites Chesapeake - Portsmouth
2.5 star property
6.4 out of 10, (335)
"Everything was great except the water pressure in the sink."
The price is NZ$164
per night
25 Jun - 26 Jun
Sleep Inn & Suites Chesapeake - Portsmouth
Hilton Garden Inn Suffolk Riverfront
3.0 star property
8.4 out of 10, Very good, (676)
"The rooms were renovated, clean and spacious. The staff was professional and helpful. The Riverfront was peaceful and relaxing. "
The price is NZ$237
per night
30 Jun - 1 Jul
Hilton Garden Inn Suffolk Riverfront
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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?

Welcome to Carrollton: This holiday home rental outside of Windsor offers 1 hot tub, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Suffolk Seaboard Station Railroad Museum, or get out into nature at a spot like Lake Prince. In the wider area, you’ll find Planters Peanut Center and Suffolk Center for Cultural Arts.

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.

Recent reviews of Windsor properties
Expedia verified reviews