Windsor Vacation Rentals

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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Windsor

Historic Cottage - At Hopelands Gardens close to Hitchcock Woods (Remodeled)
Property grounds

Historic Cottage - At Hopelands Gardens close to Hitchcock Woods (Remodeled)

10.0 out of 10, Exceptional, (90)
"A delightful and comfortable cottage next to Hopelands Gardens and convenient for exploring the town. "
Historic Cottage - At Hopelands Gardens close to Hitchcock Woods (Remodeled)
Charming 2-bedroom cottage 3 miles from Historic downtown Aiken!
Interior

Charming 2-bedroom cottage 3 miles from Historic downtown Aiken!

$180 nightly
The price is $202
Sep 4 - Sep 5
Total with taxes and fees
Charming 2-bedroom cottage 3 miles from Historic downtown Aiken!
10 Acre Country Estate, Serene and Relaxing
Exterior

10 Acre Country Estate, Serene and Relaxing

9.0 out of 10, Wonderful, (85)
"Feels like home "
10 Acre Country Estate, Serene and Relaxing
Victory Reins- Quiet Country Stay Near Aiken, Pet Friendly,
Terrace/patio

Victory Reins- Quiet Country Stay Near Aiken, Pet Friendly,

10.0 out of 10, Exceptional, (10)
"The place was very clean and Quiet"
$324 nightly
The price is $362
Sep 4 - Sep 5
Total with taxes and fees
Victory Reins- Quiet Country Stay Near Aiken, Pet Friendly,
Beautiful 3BR Townhouse
Aerial view

Beautiful 3BR Townhouse

3.0 star property
9.4 out of 10, Exceptional, (13)
"Clean, quiet and pleasant. A great location for a private weekend away."
Beautiful 3BR Townhouse
5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.
Pool

5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.

8.8 out of 10, Excellent, (15)
"Our stay was perfect. "
$245 nightly
The price is $274
Sep 8 - Sep 9
Total with taxes and fees
5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.
2 Mi to Historic Horse District: Dog-Friendly Home
TV

2 Mi to Historic Horse District: Dog-Friendly Home

9.0 out of 10, Wonderful, (2)
"House was great, needed batteries in the smoke detector, had roaches in kitchen and bathroom. Outdoor sofa covered in hair. "
2 Mi to Historic Horse District: Dog-Friendly Home
Trotters Cottage-Close to Bruces Field and Downtown
Fridge, microwave, oven, stovetop

Trotters Cottage-Close to Bruces Field and Downtown

9.4 out of 10, Exceptional, (26)
"The small home was very nice and very clean in a local neighborhood. It was perfect for my son and myself. "
Trotters Cottage-Close to Bruces Field and Downtown
Downtown Aiken- The Collins Property
Fridge, microwave, oven, stovetop

Downtown Aiken- The Collins Property

10.0 out of 10, Exceptional, (47)
"This was the perfect spot for our family while visiting Aiken. The home was clean, comfortable, and just as advertised with plenty of space for our family of five. We wouldnt hesitate to stay here again when we’re back in the area. "
$246 nightly
The price is $276
Sep 15 - Sep 16
Total with taxes and fees
Downtown Aiken- The Collins Property
Cottage Downtown Aiken*Horse Events*Pet Friendly*Polo*Golf
Exterior

Cottage Downtown Aiken*Horse Events*Pet Friendly*Polo*Golf

10.0 out of 10, Exceptional, (79)
"The property exceeded our expectations. Plenty of room lovely and made us feel right at home"
Cottage Downtown Aiken*Horse Events*Pet Friendly*Polo*Golf
The Loft- Downtown Aiken
Interior

The Loft- Downtown Aiken

10.0 out of 10, Exceptional, (123)
"Great spot to stay in dt aiken and walk to all the restaurants and shops."
The Loft- Downtown Aiken
Exquisite furnished rental in Downtown Aiken!
Fridge, microwave, oven, stovetop

Exquisite furnished rental in Downtown Aiken!

10.0 out of 10, Exceptional, (18)
"Great spot to stay a few days. Very nicely done remodel on a house, felt very comfortable there!"
Exquisite furnished rental in Downtown Aiken!
The stylish Gentry, just minutes from downtown Aiken and Bruce's Field.
Microwave, oven, stovetop, dishwasher

The stylish Gentry, just minutes from downtown Aiken and Bruce's Field.

9.8 out of 10, Exceptional, (21)
"This property was awesome! Very clean and just what we needed for our trip to the Masters!"
The stylish Gentry, just minutes from downtown Aiken and Bruce's Field.
Country Cottage
Property grounds

Country Cottage

9.8 out of 10, Exceptional, (13)
"Had a nice stay! Enjoyed staying at this property very clean and would stay again"
Country Cottage
A quiet place to relax, yet close to everything. Minutes from downtown.
Exterior

A quiet place to relax, yet close to everything. Minutes from downtown.

10.0 out of 10, Exceptional, (42)
"Great place, great hosts "
A quiet place to relax, yet close to everything. Minutes from downtown.
Entire Historic Home - Carolina Getaway
Exterior

Entire Historic Home - Carolina Getaway

9.8 out of 10, Exceptional, (9)
"A Solar Technician working at some nearby sites stayed in this home. He liked it so much the first time he requested it again."
$207 nightly
The price is $226
Sep 8 - Sep 9
Total with taxes and fees
Entire Historic Home - Carolina Getaway
Walk to Powderhouse Polo Fields: Aiken Getaway
Interior

Walk to Powderhouse Polo Fields: Aiken Getaway

9.6 out of 10, Exceptional, (10)
"The home was very clean and well maintained. It was also close to everything (stores, restaurants, things to do). Definitely recommend staying there!"
Walk to Powderhouse Polo Fields: Aiken Getaway
Charming 2-bedroom condo in quaint Aiken
Exterior

Charming 2-bedroom condo in quaint Aiken

10.0 out of 10, Exceptional, (4)
"Great property, beautiful apartment, very well maintained. Easy walking to shops and restaurants, great location. Highly recommended."
Charming 2-bedroom condo in quaint Aiken
Condo located downtown Aiken that's only a 5-minute walk to the Alley!
Fridge, microwave, oven, stovetop

Condo located downtown Aiken that's only a 5-minute walk to the Alley!

10.0 out of 10, Exceptional, (27)
"Ideal location downtown just 5 min walk to Alley. The place was very clean and comfortable. Nice kitchen, we cooked a few meals. "
Condo located downtown Aiken that's only a 5-minute walk to the Alley!
Barnwell Estate
Smart TV, fireplace

Barnwell Estate

9.8 out of 10, Exceptional, (6)
"I was in Aiken for a golf weekend with friends and we loved staying at Tim’s house. It was a great location (walkable) to downtown and very close to tons of great golf courses in and around Aiken. We look forward to staying there again! "
$1,004 nightly
The price is $1,124
Sep 15 - Sep 16
Total with taxes and fees
Barnwell Estate
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $202 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals near the most popular points of interest in Windsor, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental in Windsor?

5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.: Visitors like this Windsor vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

Expedia has 4 vacation rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as God's Acre Healing Springs, or get out into nature at a spot like Aiken State Park. Aiken Gopher Tortoise Heritage Preserve and Aiken Mall are a couple of places you'll find in the larger area.

What’s a vacation rental in Windsor like?

A vacation rental is a private property you can stay in for a long or short time in Windsor. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family gatherings.