Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 CA $195
CA $294 total
includes taxes & fees
May 12 - May 13
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Palmer Room at The Inn

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 CA $195
CA $293 total
includes taxes & fees
May 10 - May 11
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Sutton Room at The Inn

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 CA $430
CA $681 total
includes taxes & fees
May 10 - May 11
Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122

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 CA $430
CA $681 total
includes taxes & fees
May 10 - May 11
Luxury 3 Bedroom Home, Arnold Palmer Occano Coastal Club, Villa 118

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 CA $504
CA $773 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 116

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 CA $504
CA $773 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 114

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 CA $568
CA $856 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom House, Arnold Palmer Occano Coastal Club, The Capehart

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 CA $211
CA $312 total
includes taxes & fees
May 10 - May 11
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Reider Room at The Inn

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 CA $568
CA $856 total
includes taxes & fees
Jun 7 - Jun 8
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn

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 CA $195
CA $293 total
includes taxes & fees
May 10 - May 11
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Avoca Room at The Inn

Reconnect with nature at this unforgettable escape.

Reconnect with nature at this unforgettable escape.
Columbia
The price is CA $75
CA $185 total
includes taxes & fees
May 10 - May 11
Reconnect with nature at this unforgettable escape.

Warm & Comfortable Stay

Warm & Comfortable Stay
Princeville
The price is CA $166
CA $218 total
includes taxes & fees
May 16 - May 17
Warm & Comfortable Stay

The little cabin on the mountainside

The little cabin on the mountainside
Edenton
10.0 out of 10, Exceptional, (204 reviews)
"The stay was wonderful, beautiful house and property! "
United States
Logan J.
The price is CA $225
CA $399 total
includes taxes & fees
May 10 - May 11
The little cabin on the mountainside

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 CA $225
CA $488 total
includes taxes & fees
May 12 - May 13
No Say Left Farm

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 CA $184
CA $368 total
includes taxes & fees
May 9 - May 10
Inner Banks Condo With Golf Course and Marina Access

Cheerful 2-bedroom Edenton bungalow getaway

Cheerful 2-bedroom Edenton bungalow getaway
Edenton
9.8 out of 10, Exceptional, (90 reviews)
"The bungalow was very comfortable, clean and cozy. We had a great time!!"
United States
Nanette S.
The price is CA $148
CA $308 total
includes taxes & fees
May 10 - May 11
Cheerful 2-bedroom Edenton bungalow getaway

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 CA $157
CA $260 total
includes taxes & fees
May 9 - May 10
Charming new in 2026 private apartment on the water in lovely Edenton.

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 CA $225
CA $488 total
includes taxes & fees
May 10 - May 11
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

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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.