Windsor Vacation Rentals

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Vacation Rentals in Windsor

Microwave, oven, stovetop, dishwasher
Welcome to Carrollton
10.0 out of 10, Exceptional, (5)
"Very comfortable house with large rooms and plenty of space throughout the home. The spaces in the main rooms provided plenty of space for our work meetings and allowed to work in small groups for discussions. Definitely recommend this house for large numbered families or for off-site work related group meetings. Highly recommend if anyone is looking for a quiet and peaceful residence to enjoy, this home in this quiet residential neighborhood would be a great one to consider."
Welcome to Carrollton
Fridge, microwave, stovetop, coffee/tea maker
Guesthouse in ideal location with private entrance
10.0 out of 10, Exceptional, (1)
"Nearby outdoor track. Friendly neighbors. Very nice"
The price is CA $130
CA $307 total
includes taxes & fees
May 27 - May 28
Guesthouse in ideal location with private entrance
Fridge, microwave, oven, stovetop
Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.
10.0 out of 10, Exceptional, (17)
"We came from Tennessee, Illinois, Maryland and Virginia to be in Portsmouth VA for our granddaughter’s wedding. “Paradise House” was the perfect place for us. Spacious, beautiful and comfortable. TVs in almost every room but we didn’t use them. The neighbors were friendly, the sun was shining and we thoroughly enjoyed our stay."
Beautiful 4bedroom vacation pool home, where relaxation & indulgence intertwine.
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Private kitchen
HOME AWAY FROM HOME
10.0 out of 10, Exceptional, (2)
"Communicate with properly manager whats A1"
HOME AWAY FROM HOME
Exterior
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
10.0 out of 10, Exceptional, (22)
"Wonderful stay."
The price is CA $172
CA $239 total
includes taxes & fees
May 27 - May 28
Home AWAY FROM HOME!!! Franklin, VA<br>(1 BEDROOM)
Fridge, microwave, stovetop, coffee/tea maker
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
Interior
Luxury Home close to Rivers Casino and Va Beach!
Luxury Home close to Rivers Casino and Va Beach!
Property grounds
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.
Fridge, microwave, oven, stovetop
Cozy Townhome
Cozy Townhome
Fridge, microwave, stovetop, dishwasher
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!
Fridge, microwave, oven, stovetop
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."
Experience Chesapeake Your Way and Relax with Golf Entire home
Living area
Private Guest Suite in Historic house
Private Guest Suite in Historic house
Iron/ironing board, WiFi, bed sheets
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
Property grounds
Peace on the Brewers River.
10.0 out of 10, Exceptional, (42)
"My family and I had a wonderful four night stay. This home is very clean, beautiful, and is furnished with everything you need to feel at home. There were even fresh flowers and warm homemade bread when we arrived! We would definitely stay there again ! The hosts are amazing to work with"
Peace on the Brewers River.
Fridge, microwave, stovetop, dishwasher
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!
1 bedroom, iron/ironing board, WiFi, bed sheets
The Mermaids Lair 🧜‍♀️
8.0 out of 10, Very good, (4)
"Nice waterfront spot, bed was comfy"
The Mermaids Lair 🧜‍♀️
Property grounds
Bright Chesapeake Home Near Shopping & Dining
3.0 star property
Bright Chesapeake Home Near Shopping & Dining
Exterior
The Vine--4 Bedrooms
10.0 out of 10, Exceptional, (6)
"Jasmine was the perfect host. Great communication and beautiful home away from home. She was available and ready to assist with anything I needed to ensure that my stay was great. We will be back!"
The Vine--4 Bedrooms
Interior
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 CA $185
CA $329 total
includes taxes & fees
May 25 - May 26
THE"HAVEN" (1 BEDROOM)
Interior
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 CA $275
CA $414 total
includes taxes & fees
May 25 - May 26
The "KINGSDALE" 2 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

Desk, iron/ironing board, free WiFi, bed sheets
Sleep Inn & Suites Chesapeake - Portsmouth
2.5 star property
6.4 out of 10, (327)
"Small room (small tv too!) but clean and comfortable room! Only complaint was it was a full size mattress in a queen size bed frame so it was VERY small but luckily we are a couple who cuddles lol. But the bed was really comfortable and I slept great. "
The price is CA $108
CA $130 total
includes taxes & fees
May 27 - May 28
Sleep Inn & Suites Chesapeake - Portsmouth
Exterior
Comfort Suites Suffolk - Chesapeake
2.5 star property
7.8 out of 10, Good, (1000)
"Good service"
The price is CA $138
CA $159 total
includes taxes & fees
Jun 23 - Jun 24
Comfort Suites Suffolk - Chesapeake
Exterior
Hilton Garden Inn Suffolk Riverfront
3.0 star property
8.4 out of 10, Very good, (668)
"It was just a very cozy environment "
The price is CA $174
CA $199 total
includes taxes & fees
May 27 - May 28
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we give you a choice of vacation rentals close to well known points of interest in Windsor, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Windsor has to offer?

Welcome to Carrollton: Visitors like this Windsor vacation home rental. It offers a spa tub, a barbecue grill, 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 larger area, you’ll find Planters Peanut Center and Suffolk Center for Cultural Arts.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.

Recent reviews of Windsor properties
Expedia verified reviews