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Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

1. Charming 2-bedroom cabin with AC, WiFi in serene Jamesville

Charming 2-bedroom cabin with AC, WiFi in serene Jamesville
Jamesville
9.8 out of 10, Exceptional, (10 reviews)
"The cabin was extremely clean and well maintained. The property owner was cordial and quick to respond to any questions we had. I would definitely recommend this property. "
United States
Melisa B.
The price is NZ$438
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom cabin with AC, WiFi in serene Jamesville

2. King Bed|Smoking|Williamston

King Bed|Smoking|Williamston
Williamston NC
10.0 out of 10, Exceptional, (51 reviews)
"Had fun exploring nearby museums while enjoying this convenient lodging option, worth every penny spent on our trip!"
United States
Anonymous traveller
The price is NZ$118
includes taxes & fees
9 Nov - 10 Nov
King Bed|Smoking|Williamston

3. The little cabin on the mountainside

The little cabin on the mountainside
Edenton
10.0 out of 10, Exceptional, (214 reviews)
"Super adorable property with amazing owners! They are friendly and charming! The fishing was great! We caught spot, croaker, white perch, catfish, and a couple crabs!! We will definitely return!!"
United States
Kasi L.
The price is NZ$552
includes taxes & fees
14 Nov - 15 Nov
The little cabin on the mountainside

4. King Bed Non Smoking

King Bed Non Smoking
Williamston NC
10.0 out of 10, Exceptional, (53 reviews)
"Perfectly adequate stay with all basics covered, just felt like home away from home."
United States
Anonymous traveller
The price is NZ$118
includes taxes & fees
9 Nov - 10 Nov
King Bed Non Smoking

5. 2 Full Beds | Williamston

2 Full Beds | Williamston
Williamston NC
10.0 out of 10, Exceptional, (55 reviews)
"The location is convenient near local attractions with an easy drive to museums around Williamston,great for sightseeing!"
United States
Anonymous traveller
The price is NZ$128
includes taxes & fees
19 Nov - 20 Nov
2 Full Beds | Williamston

6. 2 Full Bed|Smoking|Williamston

2 Full Bed|Smoking|Williamston
Williamston NC
10.0 out of 10, Exceptional, (52 reviews)
"WiFi worked well for browsing and planning activities during our stay."
United States
Anonymous traveller
The price is NZ$128
includes taxes & fees
9 Nov - 10 Nov
2 Full Bed|Smoking|Williamston

7. Steps to Downtown! Family Home in Historic Edenton

Steps to Downtown! Family Home in Historic Edenton
3.0 star property
Edenton Historic District
The price is NZ$552
includes taxes & fees
9 Nov - 10 Nov
Steps to Downtown! Family Home in Historic Edenton

8. Cheerful 2-bedroom Edenton bungalow getaway

Cheerful 2-bedroom Edenton bungalow getaway
Edenton
9.8 out of 10, Exceptional, (114 reviews)
"Wonderful stay!"
United States
lindsay m.
The price is NZ$446
includes taxes & fees
9 Nov - 10 Nov
Cheerful 2-bedroom Edenton bungalow getaway

9. Steps to Downtown! Family Home in Historic Edenton

Steps to Downtown! Family Home in Historic Edenton
Edenton Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Great place, close to downtown and very clean, host communicated very well"
United States
Chris M.
The price is NZ$534
includes taxes & fees
9 Nov - 10 Nov
Steps to Downtown! Family Home in Historic Edenton

10. Edenton Historic District, Walk Downtown, Dogs Welcome, Fenced Yard!

Edenton Historic District, Walk Downtown, Dogs Welcome, Fenced Yard!
Edenton Historic District
10.0 out of 10, Exceptional, (69 reviews)
"Wonderful property. Great stay."
United States
Nick R.
The price is NZ$657
includes taxes & fees
9 Nov - 10 Nov
Edenton Historic District, Walk Downtown, Dogs Welcome, Fenced Yard!

11. Charming new in 2026 private apartment on the water in lovely Edenton.

Charming new in 2026 private apartment on the water in lovely Edenton.
Edenton
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful stay on this beautiful property, it was very clean and the Host provided everything we need. we truly enjoyed our stay. I highly recommend this property."
United States
Ronald R.
The price is NZ$327
includes taxes & fees
9 Nov - 10 Nov
Charming new in 2026 private apartment on the water in lovely Edenton.

12. No Say Left Farm

No Say Left Farm
Cofield
9.8 out of 10, Exceptional, (10 reviews)
"The host is quick to respond with questions! Lots of room and sleep area! Very clean and comfortable beds!"
United States
Melissa W.
The price is NZ$598
includes taxes & fees
7 Dec - 8 Dec
No Say Left Farm

13. No Say Right Farm

No Say Right Farm
Cofield
10.0 out of 10, Exceptional, (4 reviews)
"If you like quietness, this is the place for you. A place to stay for a full week. "
United States
Jackie M.
The price is NZ$598
includes taxes & fees
7 Dec - 8 Dec
No Say Right Farm

14. Reconnect with nature at this unforgettable escape.

Reconnect with nature at this unforgettable escape.
Columbia
The price is NZ$260
includes taxes & fees
3 Dec - 4 Dec
Reconnect with nature at this unforgettable escape.

15. Spacious 4-bedroom house in Creswell NC right on Lake Phelps.

Spacious 4-bedroom house in Creswell NC right on Lake Phelps.
Creswell
The price is NZ$497
includes taxes & fees
1 Dec - 2 Dec
Spacious 4-bedroom house in Creswell NC right on Lake Phelps.

16. Heaven on the River, A Tranquil Home, Boaters Paradise, Fishing, Swimming

Heaven on the River, A Tranquil Home, Boaters Paradise, Fishing, Swimming
Hertford
9.8 out of 10, Exceptional, (10 reviews)
"Host communication was very fast - check in and out went smoothly: lovely home to stay and hot tub was great to have on site"
United States
Danyelle M.
The price is NZ$383
includes taxes & fees
11 Nov - 12 Nov
Heaven on the River, A Tranquil Home, Boaters Paradise, Fishing, Swimming
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

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?

"Country Farm House" : This highly rated holiday home rental in Windsor is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Windsor?

Expedia has 7 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 Roanoke River Lighthouse and Maritime Museum, or get out into nature at a spot like Albemarle Sound. In the wider area, you’ll find Senator Bob Martin Eastern Agricultural Center and Deadwood.

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 amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.