Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Windsor vacation rentals

Property grounds

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Palmer Room at The Inn

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Palmer Room at The Inn
Merry Hill
The price is ￥22,447
￥33,675 total
includes taxes & fees
May 13 - May 14
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Palmer Room at The Inn
Property grounds

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Sutton Room at The Inn

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Sutton Room at The Inn
Merry Hill
The price is ￥22,374
￥33,566 total
includes taxes & fees
May 13 - May 14
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Sutton Room at The Inn
Golf

Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122

Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122
Windsor
The price is ￥49,354
￥77,934 total
includes taxes & fees
May 14 - May 15
Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122
Golf

Luxury 3 Bedroom Home, Arnold Palmer Occano Coastal Club, Villa 118

Luxury 3 Bedroom Home, Arnold Palmer Occano Coastal Club, Villa 118
Windsor
The price is ￥49,354
￥78,437 total
includes taxes & fees
May 14 - May 15
Luxury 3 Bedroom Home, Arnold Palmer Occano Coastal Club, Villa 118
Golf

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 116

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 116
Merry Hill
The price is ￥57,909
￥88,272 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 116
Golf

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 114

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 114
Merry Hill
The price is ￥57,909
￥89,446 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 114
Terrace/patio

Luxury 4 Bedroom House, Arnold Palmer Occano Coastal Club, The Capehart

Luxury 4 Bedroom House, Arnold Palmer Occano Coastal Club, The Capehart
Merry Hill
The price is ￥65,148
￥97,459 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom House, Arnold Palmer Occano Coastal Club, The Capehart
Property grounds

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Reider Room at The Inn

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Reider Room at The Inn
Merry Hill
The price is ￥24,184
￥35,944 total
includes taxes & fees
May 13 - May 14
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Reider Room at The Inn
Property grounds

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn
Merry Hill
6.0 out of 10, (1 review)
"Washing machine brokenMinimal kitchen untensils (no restaurants close )Was unaware the rooms are adjacent to the office area. Employees are able to walk around the living space. Each room has an individual key. This information should be shared with renters. "
United States
Trey S.
The price is ￥65,148
￥98,634 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn
1 bedroom, iron/ironing board, free WiFi, bed sheets

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Avoca Room at The Inn

1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Avoca Room at The Inn
Merry Hill
8.0 out of 10, Very Good, (1 review)
"Check in was a bit confusing only because since we were there during off season, there wasn't anyone to talk to except at the gate. We were very reluctant to just walk in to a condo. Not too much of a big deal but a few signs would have helped a little more. Very comfortable although when it said it sleeps 4 we thought that a couch or foldout bed was going to be available. The 2 bed could indeed sleep 4.Every place has different amenities, so perhaps unfair to say but... A little bit more coffee...
United States
BC S.
The price is ￥22,374
￥33,566 total
includes taxes & fees
May 13 - May 14
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Avoca Room at The Inn
Interior

Reconnect with nature at this unforgettable escape.

Reconnect with nature at this unforgettable escape.
Columbia
The price is ￥8,617
￥21,198 total
includes taxes & fees
May 16 - May 17
Reconnect with nature at this unforgettable escape.
Internet, bed sheets

Warm & Comfortable Stay

Warm & Comfortable Stay
Princeville
The price is ￥19,037
￥25,052 total
includes taxes & fees
May 20 - May 21
Warm & Comfortable Stay
Exterior

The little cabin on the mountainside

The little cabin on the mountainside
Edenton
10.0 out of 10, Exceptional, (205 reviews)
"The stay was wonderful, beautiful house and property! "
United States
Logan J.
The price is ￥25,852
￥46,103 total
includes taxes & fees
May 14 - May 15
The little cabin on the mountainside
Exterior

No Say Left Farm

No Say Left Farm
Cofield
9.6 out of 10, Exceptional, (5 reviews)
"The property was perfect! We will definitely be staying again!!!"
United States
Katie R.
The price is ￥25,852
￥56,185 total
includes taxes & fees
May 20 - May 21
No Say Left Farm
Smart TV

Inner Banks Condo With Golf Course and Marina Access

Inner Banks Condo With Golf Course and Marina Access
Hertford
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and perfect for a couples"
United States
Richard J.
The price is ￥21,152
￥42,399 total
includes taxes & fees
May 16 - May 17
Inner Banks Condo With Golf Course and Marina Access
Fridge, microwave, oven, dishwasher

Cheerful 2-bedroom Edenton bungalow getaway

Cheerful 2-bedroom Edenton bungalow getaway
Edenton
9.8 out of 10, Exceptional, (91 reviews)
"The bungalow was very comfortable, clean and cozy. We had a great time!!"
United States
Nanette S.
The price is ￥16,921
￥35,719 total
includes taxes & fees
May 24 - May 25
Cheerful 2-bedroom Edenton bungalow getaway
Terrace/patio

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
9.8 out of 10, Exceptional, (6 reviews)
The price is ￥18,050
￥29,799 total
includes taxes & fees
May 13 - May 14
Charming new in 2026 private apartment on the water in lovely Edenton.
Dining

No Say Right Farm

No Say Right Farm
Cofield
10.0 out of 10, Exceptional, (3 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 ￥25,852
￥56,185 total
includes taxes & fees
May 20 - May 21
No Say Right Farm
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

Holiday Inn Express Williamston by IHG

Holiday Inn Express Williamston by IHG

4/10 Poor
"When I first walked in it was so freaking hot in the main floor. There was no one at the front for check in. I stood there for 15 minutes before the girl came up to the front. At 5:30 in the morning the fire alarm went off and , before I could get to the first floor it had stopped. I went to the front desk and the girl with no personality goes the kitchen got to smoky. Come back to my room that night and the AC was blowing hot air , so I had to go back down stairs to as for a new room."
Karen 2-night trip
Posted 9 hours ago
Holiday Inn Express Williamston by IHG

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
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  • 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 vacation rental in Windsor?

Yes, you can find vacation rentals close to the most popular local attractions in Windsor, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Windsor has to offer?

East of Edenton! Romantic sunset waterfront getaway on the Albemarle Sound!: This vacation home rental near Windsor is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Windsor?

Expedia has 10 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 Roanoke River Lighthouse and Maritime Museum, or get out into nature at a spot like Albemarle Sound. In the larger area, you’ll find Senator Bob Martin Eastern Agricultural Center and Deadwood.

What’s a vacation rental in Windsor like?

A vacation rental is a private property where you can stay for several days or longer in Windsor. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips.