Windsor Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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
$198 nightly
The price is $222
May 12 - May 13
Total with taxes and fees
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
$190 nightly
The price is $213
May 10 - May 11
Total with taxes and fees
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
$440 nightly
The price is $494
May 7 - May 8
Total with taxes and fees
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
$446 nightly
The price is $501
May 7 - May 8
Total with taxes and fees
Luxury 3 Bedroom Home, Arnold Palmer Occano Coastal Club, Villa 118
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
$618 nightly
The price is $694
May 10 - May 11
Total with taxes and fees
Luxury 4 Bedroom House, Arnold Palmer Occano Coastal Club, The Capehart
Golf

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

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 116
Merry Hill
$558 nightly
The price is $627
May 10 - May 11
Total with taxes and fees
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
$566 nightly
The price is $635
May 10 - May 11
Total with taxes and fees
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, Villa 114
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
$202 nightly
The price is $227
May 10 - May 11
Total with taxes and fees
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Reider Room at The Inn
Property grounds

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.
$190 nightly
The price is $213
May 10 - May 11
Total with taxes and fees
1 Bedroom Suite, Arnold Palmer Occano Coastal Club, Avoca 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.
$626 nightly
The price is $702
May 12 - May 13
Total with taxes and fees
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn
Interior

Reconnect with nature at this unforgettable escape.

Reconnect with nature at this unforgettable escape.
Columbia
$120 nightly
The price is $135
May 7 - May 8
Total with taxes and fees
Reconnect with nature at this unforgettable escape.
Internet, bed sheets

Warm & Comfortable Stay

Warm & Comfortable Stay
Princeville
$142 nightly
The price is $160
May 13 - May 14
Total with taxes and fees
Warm & Comfortable Stay
Exterior

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.
$275 nightly
The price is $294
May 7 - May 8
Total with taxes and fees
The little cabin on the mountainside
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.
$240 nightly
The price is $271
May 7 - May 8
Total with taxes and fees
Inner Banks Condo With Golf Course and Marina Access
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.
$326 nightly
The price is $359
May 7 - May 8
Total with taxes and fees
No Say Left Farm
Balcony view

Waterside Resort

Waterside Resort
3.5 star property
Roper
9.4 out of 10, Exceptional, (41 reviews)
"Love the kitchen, everything you would need."
United States
Michele
$202 nightly
The price is $239
May 8 - May 9
Total with taxes and fees
Waterside Resort
Fridge, microwave, oven, dishwasher

Cheerful 2-bedroom Edenton bungalow getaway

Cheerful 2-bedroom Edenton bungalow getaway
Edenton
9.8 out of 10, Exceptional, (88 reviews)
"The bungalow was very comfortable, clean and cozy. We had a great time!!"
United States
Nanette S.
$201 nightly
The price is $225
May 7 - May 8
Total with taxes and fees
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)
$172 nightly
The price is $192
May 7 - May 8
Total with taxes and fees
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.
$326 nightly
The price is $359
May 7 - May 8
Total with taxes and fees
No Say Right Farm
Exterior

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, (62 reviews)
"We had a wouderful stay and the property was very clean and neat. Nicole was a wounderful host and made sure we had everything we needed and responded back to us very quickly with any question we had. "
United States
gregg p.
Edenton Historic District, Walk Downtown, Dogs Welcome, Fenced Yard!
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

Quality Inn Williamston

Quality Inn Williamston

10/10 Excellent
"Friendly staff, quiet location, clean rooms. Good value for mid-level hotel."
Donna 1-night trip
Posted 2 hours ago
Quality Inn Williamston

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 $135 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.

Explore a world of travel with Expedia

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?

Waterfront Home with Pier on Albemarle Beach: This vacation home rental near Windsor is located on the waterfront and has a patio, a selection of games, and a barbecue grill 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.

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.