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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation rentals

An aerial view of a property with a central building surrounded by a fenced area, trees, and a dirt road.

1. Peaceful Country Retreat Near The Masters

Peaceful Country Retreat Near The Masters
Windsor
$273 nightly
The price is $306
Oct 7 - Oct 8
Total with taxes and fees
Peaceful Country Retreat Near The Masters
A kitchen with a bar area, wooden cabinets, and a large mirror.

2. Relaxing Beautiful Views Plenty of Back Roads to Ride ATVs-Horses- Pets Welcomed

Relaxing Beautiful Views Plenty of Back Roads to Ride ATVs-Horses- Pets Welcomed
Aiken
$151 nightly
The price is $169
Oct 27 - Oct 28
Total with taxes and fees
Relaxing Beautiful Views Plenty of Back Roads to Ride ATVs-Horses- Pets Welcomed
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a brick backsplash.

3. Victory Reins- Quiet Country Stay Near Aiken, I-20 + Parking, Golf, Pets Welcome

Victory Reins- Quiet Country Stay Near Aiken, I-20 + Parking, Golf, Pets Welcome
Wagener
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and really well appointed. Check in was a breeze and it was a very nice base to enjoy our daughter’s graduation. Thanks for a wonderful stay! "
United States
Nicole O.
$423 nightly
The price is $474
Oct 4 - Oct 5
Total with taxes and fees
Victory Reins- Quiet Country Stay Near Aiken, I-20 + Parking, Golf, Pets Welcome
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

4. 5 Mi to Dtwn Aiken! Family Home w/ Open Yard

5 Mi to Dtwn Aiken! Family Home w/ Open Yard
3.0 star property
Aiken
$279 nightly
The price is $312
Oct 3 - Oct 4
Total with taxes and fees
5 Mi to Dtwn Aiken! Family Home w/ Open Yard
A compact RV interior with a kitchenette, a dining area, and a window with curtains.

5. Cozy Airstream "The Silver Saddle" unique stay in Aiken SC

Cozy Airstream "The Silver Saddle" unique stay in Aiken SC
Aiken
10.0 out of 10, Exceptional, (1 review)
"The airstream was exactly as shown in pictures. We were given code prior to checkin and everything went smoothly. Very clean and nicely decorated. The snacks and drinks were very much appreciated. 4 stars given for the expense but it's understandable the price since it is the Masters week and everything is more expensive this week. Definitely recommend the Silver Saddle."
United States
Marcia Lynn M.
$154 nightly
The price is $172
Oct 12 - Oct 13
Total with taxes and fees
Cozy Airstream "The Silver Saddle" unique stay in Aiken SC
A modern kitchen with a central island, bar stools, a dining table set for six, and a chandelier.

6. Cheerful spacious home-5 min to Bruce's Field/Downtown

Cheerful spacious home-5 min to Bruce's Field/Downtown
Aiken
10.0 out of 10, Exceptional, (25 reviews)
"One of the best places we've stayed. Beautifully kept, tons of space, family and pet friendly, and in great access to Aiken activities. Thank you for an awesome stay!"
United States
Mary S.
$559 nightly
The price is $626
Oct 4 - Oct 5
Total with taxes and fees
Cheerful spacious home-5 min to Bruce's Field/Downtown
A kitchenette with a coffee maker, mugs, a coffee pot, and a tray with sugar and creamers.

7. The Cottage on Boundary

The Cottage on Boundary
Aiken
10.0 out of 10, Exceptional, (3 reviews)
"The cottage was absolutely beautiful it was so cozy, with everything you would possibly need, the owners thought of everything to make your stay amazing."
United States
Tina M.
$313 nightly
The price is $350
Oct 27 - Oct 28
Total with taxes and fees
The Cottage on Boundary
A two-story house with a front porch, a black door, and the number 310 on the front.

8. New! Clean, bright cottage walking distance to downtown Aiken!

New! Clean, bright cottage walking distance to downtown Aiken!
Aiken
10.0 out of 10, Exceptional, (3 reviews)
"A great place to stay within walking distance if the historic downtown area."
United States
Robert H.
$299 nightly
The price is $335
Oct 4 - Oct 5
Total with taxes and fees
New! Clean, bright cottage walking distance to downtown Aiken!
A hallway with a wooden floor, white walls, a white door, and a ceiling light fixture.

9. Saddle up, Tee off! Luxury King in Horse Country

Saddle up, Tee off! Luxury King in Horse Country
Aiken
10.0 out of 10, Exceptional, (1 review)
$515 nightly
The price is $577
Oct 8 - Oct 9
Total with taxes and fees
Saddle up, Tee off! Luxury King in Horse Country
A spacious barn with multiple stalls, a green door, and a concrete floor.

10. Mimosa Cottage and Farm- 2br cottage & stalls. Masters

Mimosa Cottage and Farm- 2br cottage & stalls. Masters
Aiken
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place, especially if you have horses with you. Beautiful paddocks and stalls. The cottage itself is very clean and cute, host is very easy to work with."
United States
Amanda M.
$305 nightly
The price is $342
Oct 3 - Oct 4
Total with taxes and fees
Mimosa Cottage and Farm- 2br cottage & stalls. Masters
A modern kitchen with white cabinets, stainless steel appliances, a wooden island with bar stools, and a tiled backsplash.

11. Bluebell Cottage - Renovated, No Checkout Instructions, Close to Downtown

Bluebell Cottage - Renovated, No Checkout Instructions, Close to Downtown
Aiken
10.0 out of 10, Exceptional, (8 reviews)
"The owners were easy to deal with and made stay a pleasure "
United States
Torrey H.
$348 nightly
The price is $390
Oct 7 - Oct 8
Total with taxes and fees
Bluebell Cottage - Renovated, No Checkout Instructions, Close to Downtown
A house with a black front door, a number '133' on the wall, and a small porch with steps.

12. Historic charm near downtown/Bruce's Field

Historic charm near downtown/Bruce's Field
Aiken
10.0 out of 10, Exceptional, (24 reviews)
"Nice property."
United States
John H.
$422 nightly
The price is $473
Oct 7 - Oct 8
Total with taxes and fees
Historic charm near downtown/Bruce's Field
A modern kitchen with a black and gold color scheme, featuring a double sink, a refrigerator, and a bar area with stools.

13. Downtown Aiken Elegant NEW Home

Downtown Aiken Elegant NEW Home
Aiken
9.8 out of 10, Exceptional, (28 reviews)
"Owners were great and made stay enjoyable "
United States
Torrey H.
$367 nightly
The price is $411
Oct 12 - Oct 13
Total with taxes and fees
Downtown Aiken Elegant NEW Home
A residential property with a grassy yard, a wooden staircase leading to a porch, and a white building in the background.

14. 5 Mi to Dtwn Aiken! Family Home w/ Open Yard

5 Mi to Dtwn Aiken! Family Home w/ Open Yard
Aiken
$283 nightly
The price is $317
Oct 3 - Oct 4
Total with taxes and fees
5 Mi to Dtwn Aiken! Family Home w/ Open Yard
A room with a wooden dining table, a white desk with a chair, a brown sofa, and a door leading to another room.

15. Golfers Oasis Centrally Located

Golfers Oasis Centrally Located
Aiken
10.0 out of 10, Exceptional, (1 review)
"House was perfect for a quick trip to play golf. Very clean and well kept. Would definitely stay again. "
United States
Joseph F.
$319 nightly
The price is $357
Oct 26 - Oct 27
Total with taxes and fees
Golfers Oasis Centrally Located
Outdoor dining

16. Soothing 2-bedroom house with AC in charming Aiken

Soothing 2-bedroom house with AC in charming Aiken
Aiken
$790 nightly
The price is $885
Oct 3 - Oct 4
Total with taxes and fees
Soothing 2-bedroom house with AC in charming Aiken
A spacious hallway with hardwood flooring, white walls, and a ceiling light fixture.

17. Downtown Aiken- The Collins Property

Downtown Aiken- The Collins Property
Aiken
9.8 out of 10, Exceptional, (90 reviews)
"Loved our stay. Would book again!"
United States
Jennifer R.
$235 nightly
The price is $263
Oct 6 - Oct 7
Total with taxes and fees
Downtown Aiken- The Collins Property
A dining table set with plates, glasses, and a vase with flowers.

18. Quaint house, king bed 2min from down town

Quaint house, king bed 2min from down town
Aiken
10.0 out of 10, Exceptional, (1 review)
"Great house and in a very convenient location. "
United States
Creg F.
$564 nightly
The price is $572
Oct 5 - Oct 6
Total with taxes and fees
Quaint house, king bed 2min from down town
A spacious living room with hardwood floors, a blue sofa, a coffee table, and a fireplace.

19. 4BR + Putting Green | Fenced Yard | No Checkout Chores

4BR + Putting Green | Fenced Yard | No Checkout Chores
Aiken
10.0 out of 10, Exceptional, (50 reviews)
"The host communicated well, gave all details throughout the whole process making it the easiest rental we’ve ever stayed at!"
United States
Melissa L.
$395 nightly
The price is $442
Oct 5 - Oct 6
Total with taxes and fees
4BR + Putting Green | Fenced Yard | No Checkout Chores
A kitchen with white cabinets, a black door, and a ceiling fan.

20. Pet Friendly • Fenced Yard • Putting Green

Pet Friendly • Fenced Yard • Putting Green
Aiken
10.0 out of 10, Exceptional, (72 reviews)
"This is a cute and nice home to stay! Activities are provided and hosts are super fast with communication!! 10/10!"
United States
Jennifer M.
$298 nightly
The price is $334
Oct 7 - Oct 8
Total with taxes and fees
Pet Friendly • Fenced Yard • Putting Green
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

Aiken Midtown Hotel

Aiken Midtown Hotel

10/10 Excellent
"Clean room and great front desk service. A pleasure"
Michael 2-night trip
Posted 23 hours ago
Aiken Midtown Hotel

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 $192 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.

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?

Downtown Aiken- The Collins Property: Visitors like this Windsor vacation home rental. It is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

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 Cedar Creek 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.