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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday rentals

A kitchen with wooden flooring, a central island, dark cabinets, a sink, and a window.

1. Peaceful Country Retreat Near The Masters

Peaceful Country Retreat Near The Masters
Windsor
The price is HK$1,247
HK$2,091 total
includes taxes & fees
2 Nov - 3 Nov
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
The price is HK$1,024
HK$1,323 total
includes taxes & fees
1 Nov - 2 Nov
Relaxing Beautiful Views Plenty of Back Roads to Ride ATVs-Horses- Pets Welcomed
A kitchen with white cabinets, a stainless steel refrigerator, a dining table with a woven table runner, and a wall-mounted clock.

3. The Cottage on Boundary

The Cottage on Boundary
Aiken
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$1,130
HK$2,706 total
includes taxes & fees
2 Nov - 3 Nov
The Cottage on Boundary
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a brick backsplash.

4. 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)
"Great stay"
United States
MATTHEW H.
The price is HK$1,961
HK$3,717 total
includes taxes & fees
31 Oct - 1 Nov
Victory Reins- Quiet Country Stay Near Aiken, I-20 + Parking, Golf, Pets Welcome
Outdoor dining

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

Soothing 2-bedroom house with AC in charming Aiken
Aiken
The price is HK$5,492
HK$6,933 total
includes taxes & fees
31 Oct - 1 Nov
Soothing 2-bedroom house with AC in charming Aiken
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.
The price is HK$1,836
HK$3,831 total
includes taxes & fees
30 Nov - 1 Dec
Cheerful spacious home-5 min to Bruce's Field/Downtown
A house with a black front door, a number '133' on the wall, and a small porch with steps.

7. Historic charm near downtown/Bruce's Field

Historic charm near downtown/Bruce's Field
Aiken
10.0 out of 10, Exceptional, (26 reviews)
"Nice property."
United States
John H.
The price is HK$2,126
HK$4,024 total
includes taxes & fees
17 Nov - 18 Nov
Historic charm near downtown/Bruce's Field
A hallway with a wooden floor, white walls, a white door, and a ceiling light fixture.

8. 4BR Ranch • Sleeps 7 • Near Bruces Field • Trailer Parking • Dogs OK

4BR Ranch • Sleeps 7 • Near Bruces Field • Trailer Parking • Dogs OK
Aiken
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,872
HK$4,574 total
includes taxes & fees
3 Nov - 4 Nov
4BR Ranch • Sleeps 7 • Near Bruces Field • Trailer Parking • Dogs OK
A two-story house with a front porch, a black door, and the number 310 on the front.

9. 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, (5 reviews)
"A great place to stay within walking distance if the historic downtown area."
United States
Robert H.
The price is HK$1,138
HK$2,803 total
includes taxes & fees
1 Nov - 2 Nov
New! Clean, bright cottage walking distance to downtown Aiken!
A bedroom with a bed, bedside table, lamp, and a hallway leading to a bathroom.

10. Aiken Equestrian | Dog Friendly |Bruce's Field

Aiken Equestrian | Dog Friendly |Bruce's Field
Aiken
The price is HK$1,389
HK$3,763 total
includes taxes & fees
1 Nov - 2 Nov
Aiken Equestrian | Dog Friendly |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.

11. Downtown Aiken Elegant NEW Home

Downtown Aiken Elegant NEW Home
Aiken
9.8 out of 10, Exceptional, (29 reviews)
"Owners were great and made stay enjoyable "
United States
Torrey H.
The price is HK$1,801
HK$3,291 total
includes taxes & fees
9 Nov - 10 Nov
Downtown Aiken Elegant NEW Home
A front porch with a blue door, white columns, and two wall-mounted lanterns.

12. 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.
The price is HK$1,177
HK$2,680 total
includes taxes & fees
31 Oct - 1 Nov
Mimosa Cottage and Farm- 2br cottage & stalls. Masters
A dining table set with plates, glasses, and a vase with flowers.

13. 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.
The price is HK$1,648
HK$3,168 total
includes taxes & fees
2 Nov - 3 Nov
Quaint house, king bed 2min from down town
A spacious hallway with hardwood flooring, white walls, and a ceiling light fixture.

14. Downtown Aiken- The Collins Property

Downtown Aiken- The Collins Property
Aiken
9.8 out of 10, Exceptional, (93 reviews)
"Loved our stay. Would book again!"
United States
Jennifer R.
The price is HK$883
HK$2,078 total
includes taxes & fees
9 Nov - 10 Nov
Downtown Aiken- The Collins Property
A modern kitchen with a central island, white cabinetry, and a large window providing natural light.

15. Your perfect getaway nestled in the heart of Aiken.

Your perfect getaway nestled in the heart of Aiken.
Aiken
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for a golf trip"
United States
John S.
The price is HK$4,773
HK$8,114 total
includes taxes & fees
1 Nov - 2 Nov
Your perfect getaway nestled in the heart of Aiken.
A spacious living room with a high ceiling, exposed beams, a large sofa, a coffee table, and a staircase leading to an upper level.

16. Spacious 2-bedroom apartment in Salley near Eudora farms

Spacious 2-bedroom apartment in Salley near Eudora farms
Salley
10.0 out of 10, Exceptional, (3 reviews)
"In town for work, great place to stay!"
United States
Dakota G.
The price is HK$1,216
HK$2,302 total
includes taxes & fees
8 Nov - 9 Nov
Spacious 2-bedroom apartment in Salley near Eudora farms
A kitchen with white cabinets, a dishwasher, a sink, and a countertop with a basket of bread.

17. Two Homes Next Door - Lots of Entertainment

Two Homes Next Door - Lots of Entertainment
Aiken
10.0 out of 10, Exceptional, (20 reviews)
"Great host. Everything we expected Would stay again. "
United States
David
The price is HK$3,256
HK$6,643 total
includes taxes & fees
16 Nov - 17 Nov
Two Homes Next Door - Lots of Entertainment
A spacious living room with hardwood floors, a blue sofa, a coffee table, and a fireplace.

18. 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)
"Excellent host and very accommodating. House was just what we needed for our stay. Kids and doodle loved the fenced in backyard. Will stay here again in our next visit to the area."
United States
Brooke W.
The price is HK$1,067
HK$3,234 total
includes taxes & fees
16 Nov - 17 Nov
4BR + Putting Green | Fenced Yard | No Checkout Chores
A porch with two rocking chairs, a potted plant, and a sign reading 'Highland Cottage.'

19. Cozy 1930s Cottage · Fenced Yard for Dogs · Walk to Downtown Aiken

Cozy 1930s Cottage · Fenced Yard for Dogs · Walk to Downtown Aiken
Aiken
10.0 out of 10, Exceptional, (1 review)
"Lovely cottage with ample areas to walk our large golden retrievers! Very clean and well appointed. Tara was so easy to communicate with and provided everything we needed for our stay! I would stay there again when in Aiken. The cottage is so close to down town."
United States
Patricia D.
The price is HK$1,203
HK$2,701 total
includes taxes & fees
30 Nov - 1 Dec
Cozy 1930s Cottage · Fenced Yard for Dogs · Walk to Downtown Aiken
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.
The price is HK$981
HK$2,847 total
includes taxes & fees
23 Nov - 24 Nov
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

Clarion Inn & Suites Aiken South

Clarion Inn & Suites Aiken South

10/10 Excellent
"Clean and very nice staff"
Gail 1-night trip
Posted 8 hours ago
Clarion Inn & Suites Aiken South

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Downtown Aiken- The Collins Property: This holiday home rental outside of Windsor is located in the city centre, 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 that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Windsor?

Expedia has 4 holiday 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 wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family gatherings.