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Port Haywood Holiday Rentals

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Our top choices for Port Haywood holiday rentals

Holiday Home in Historic Downtown Cape Charles

Salt Box, One Block to the Beach
10.0 out of 10, Exceptional, (14)
"Very nice. Central to everything. "
United States
Greg D.
The price is NZ$521
includes taxes & fees
5 Jan - 6 Jan 2026
Salt Box, One Block to the Beach
9.4 out of 10, Exceptional, (46)
"Location is ideal"
United States
Christy M
The price is NZ$400
includes taxes & fees
22 Dec - 23 Dec
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.
10.0 out of 10, Exceptional, (2)
"This is a fabulous yurt stay! 3 minute drive to the beach/ bay! Very nice just with a full farm! Great for kids! "
United States
Colleen C.
The price is NZ$220
includes taxes & fees
22 Dec - 23 Dec
Yurt Campsite @ Blanchard Farm Site 2

Holiday Home in Fox Hill

Sojourn Aviators Dream on Back River
9.6 out of 10, Exceptional, (27)
"My family enjoyed the experience of staying near the water. The views were lovely! "
United States
Precious E.
The price is NZ$779
includes taxes & fees
13 Jan - 14 Jan 2026
Sojourn Aviators Dream on Back River
10.0 out of 10, Exceptional, (1)
The price is NZ$201
includes taxes & fees
24 Dec - 25 Dec
The Farm Overlook Treehouse At Blanchard Farm
10.0 out of 10, Exceptional, (3)
"Wonderful property! Well equipped, clean and convenient. "
United States
Stephanie R.
The price is NZ$785
includes taxes & fees
5 Jan - 6 Jan 2026
Family Fun-Next to Central Park-2 Blocks to Beach-Walk to Dining & Entertainment
10.0 out of 10, Exceptional, (1)
"I enjoyed staying here, solid place!"
United States
Charles B.
The price is NZ$498
includes taxes & fees
4 Jan - 5 Jan 2026
Tiny House close to the Beaches of Cape Charles

Mobile Home in Diggs

Blanchard Farm Camper Stay
10.0 out of 10, Exceptional, (4)
"Our stay at the Blanchard farm camper was great! We were very close to the beach. There was a fire pit available and we roasted smores. Joshua and his wife were great with communication! The camper was well out fitted with plates, towels, etc. Thanks so much!"
United States
Alexandra H.
The price is NZ$240
includes taxes & fees
22 Dec - 23 Dec
Blanchard Farm Camper Stay
The price is NZ$67
includes taxes & fees
22 Dec - 23 Dec
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Holiday Home in Historic Downtown Cape Charles

The Peach St. House - 1 Block to Park and Shops, close to beach!
10.0 out of 10, Exceptional, (12)
"The house was charming and the hosts were superb. And the location couldn’t be better. "
United States
Elizabeth R.
The price is NZ$853
includes taxes & fees
5 Jan - 6 Jan 2026
The Peach St. House - 1 Block to Park and Shops, close to beach!
10.0 out of 10, Exceptional, (1)
"Exactly what listing said! Was super clean and perfect for our short trip! Easy drive to and from the beach and the town of Cape Charles"
United States
Ella D.
The price is NZ$447
includes taxes & fees
22 Dec - 23 Dec
Experience Tiny Living, in Cape Charles, Va
10.0 out of 10, Exceptional, (1)
"Chip was very welcoming and had great communication and made sure we had everything we needed. The home was spotless and exceeded our expectations. The location was perfect for us. We really enjoyed the pickleball courts."
United States
Chris W.
The price is NZ$820
includes taxes & fees
7 Jan - 8 Jan 2026
1st Floor King Bed-Screened Porch-Family Friendly! Optional Resort & Golf Access
10.0 out of 10, Exceptional, (22)
"Great quiet location. Very cozy home. Great time at location. "
United States
James C.
The price is NZ$807
includes taxes & fees
22 Dec - 23 Dec
Bay Dream Believer Cottage on Beautiful East River Waterfront

Holiday Home in Historic Downtown Cape Charles

Golf cart included! 5 blocks to the beach, and in historic district!
10.0 out of 10, Exceptional, (15)
"A warm, inviting house with everything you need. Private backyard. Joel and Brittney are super responsive hosts who will make sure you have a nice stay!"
United States
Donna A.
The price is NZ$955
includes taxes & fees
6 Jan - 7 Jan 2026
Golf cart included! 5 blocks to the beach, and in historic district!
10.0 out of 10, Exceptional, (11)
"Great stay easy access to Cape Charles and the beach"
United States
andrew c.
The price is NZ$595
includes taxes & fees
22 Dec - 23 Dec
Pet Friendly Tiny Livin 3min from Cape Charles
10.0 out of 10, Exceptional, (1)
"This was a great stay, we loved everything about it. Highly recommended. We will definitely return."
United States
William
The price is NZ$459
includes taxes & fees
22 Dec - 23 Dec
Hippie Hideaway - Tiny House w/ Fire Pit & BBQ

Holiday Home in Historic Downtown Cape Charles

Anchors Aweigh
10.0 out of 10, Exceptional, (12)
"This house was the perfect location, hosts were great and we loved our stay! Beautiful property inside and out. "
United States
Kathryn T.
The price is NZ$1,058
includes taxes & fees
22 Dec - 23 Dec
Anchors Aweigh

Holiday Home in Cape Charles

Tiny House Hideaway with King sized Bed
9.6 out of 10, Exceptional, (5)
"We absolutely enjoyed our little tiny home! The property was great and the things to do close by were great! We would definitely stay again! "
United States
Leslie
The price is NZ$505
includes taxes & fees
22 Dec - 23 Dec
Tiny House Hideaway with King sized Bed
10.0 out of 10, Exceptional, (35)
"Very clean. Beds comfortable. Host very responsive nice quiet area Check in was easy as well as check out. "
United States
James R.
The price is NZ$538
includes taxes & fees
6 Jan - 7 Jan 2026
Fire Pit🔥 Walk to Town. 1st floor King Bed & Walk in Shower! Monthly Discounts!
10.0 out of 10, Exceptional, (31)
"We had a great stay. The house was perfect for a family with young children and well-equipped for our family. "
United States
Sarah M.
The price is NZ$1,005
includes taxes & fees
22 Dec - 23 Dec
Bay Creek Meets Historic Cape Charles! pool access!
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 Port Haywood Hotel Reviews

Find out more about Port Haywood

Everything you need to know about Port Haywood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Port Haywood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Port Haywood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Port Haywood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Port Haywood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Port Haywood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Port Haywood holiday rentals we have selected for you start as low as NZ$201 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Port Haywood rentals

At Expedia, we put the best Port Haywood holiday 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 Port Haywood 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 Port Haywood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Port Haywood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Port Haywood?

Yes, there are holiday rentals close to the most popular sights in Port Haywood, 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 Port Haywood has to offer?

Private, 7-acre waterfront retreat on Winter Harbor Haven: This highly rated holiday home rental in Port Haywood is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Port Haywood?

Choose from 4 Expedia holiday rentals in Port Haywood for a memorable holiday.

What can I see and do in Port Haywood?

Explore the area and family-friendly sights such as Deltaville Maritime Museum, or get out into nature at a spot like Chesapeake Bay. In the wider area, you’ll find Gwynn's Island Musuem and Cuba Island.

What are holiday rentals like in Port Haywood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Port Haywood. Holiday rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for small groups.