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Port Haywood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Port Haywood vacation rentals

A front door with a wreath, a wooden porch, and a gravel pathway.

1. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront
Mathews
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful location, host communicated well"
United States
Nicole K.
$412 nightly
The price is $454
Nov 9 - Nov 10
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a large window.

2. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Mathews
10.0 out of 10, Exceptional, (43 reviews)
"We had a great time at Baydreamin'."
United States
Crystal D.
$272 nightly
The price is $300
Nov 16 - Nov 17
Total with taxes and fees
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

3. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 8 - Nov 9
Total with taxes and fees
Campsite #3 At Blanchard Farm
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

4. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Nov 8 - Nov 9
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

5. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (35 reviews)
"We loved the 1920’s feeling to the home. The cleanliness and quiet location were exactly what we were looking for. We were just a block from the historical center and took advantage of the shops and eateries. We would definitely stay here afain"
United States
David
$311 nightly
The price is $346
Nov 8 - Nov 9
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A small, single-story house with a porch, a wooden deck, and a brick pathway.

6. Deltaville 2BR Retreat, Walk to Museum, Boat Parking

Deltaville 2BR Retreat, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was perfect - loved staying here. "
United States
John L.
$273 nightly
The price is $275
Nov 12 - Nov 13
Total with taxes and fees
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

7. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 8 - Nov 9
Total with taxes and fees
Campsite #4 At Blanchard Farm
A house with a large lawn, surrounded by tall trees.

8. Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Hayes
8.4 out of 10, Very good, (5 reviews)
"Great property. Waterfront with pier, huge yard, beautiful home with pool table, hot tub and projector set up. 100% would stay here again and recommend as would all of the family we had stay or visit us there. "
United States
Steve F.
$1,080 nightly
The price is $1,202
Nov 7 - Nov 8
Total with taxes and fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

9. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.2 out of 10, Wonderful, (27 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
$362 nightly
The price is $422
Nov 7 - Nov 8
Total with taxes and fees
Smith Beach cottage w/ private sunset
A spacious living room with a large gray sectional sofa, a wooden coffee table, and a ceiling fan. There are nautical decorations on the wall and a view of a lake through large glass doors.

10. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
9.8 out of 10, Exceptional, (52 reviews)
"This place was a perfect getaway. Quiet and a beautiful view!"
United States
David P.
$358 nightly
The price is $395
Nov 23 - Nov 24
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A covered deck with wooden chairs and tables, overlooking a marina with boats.

11. The Captain's Quarters located in Cape Charles, VA offers breathtaking views.

The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles
9.8 out of 10, Exceptional, (84 reviews)
"Very nice views of the water. Great location, close to town and restaurants."
United States
Bart
$299 nightly
The price is $340
Nov 8 - Nov 9
Total with taxes and fees
The Captain's Quarters located in Cape Charles, VA offers breathtaking views.
A covered porch with wicker furniture, a glass coffee table, and a view of the neighborhood.

12. Cape Haven - Condo 1.5 Blocks from Beach

Cape Haven - Condo 1.5 Blocks from Beach
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (51 reviews)
"Was wonderful..so close to everything..property was great ..had everything you need"
United States
Donna L.
$422 nightly
The price is $477
Nov 12 - Nov 13
Total with taxes and fees
Cape Haven - Condo 1.5 Blocks from Beach
A living room with a light blue wall, a wooden coffee table, a beige sofa with blue cushions, a wicker chair, and a patterned rug.

13. Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex

Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
Historic Downtown Cape Charles
9.8 out of 10, Exceptional, (66 reviews)
"Great house perfect for our family very conveniently located!"
United States
Dorothy A.
$450 nightly
The price is $509
Nov 17 - Nov 18
Total with taxes and fees
Across from the park and 2 blocks from beach & restaurants- LEFT side of duplex
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

14. The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
$302 nightly
The price is $333
Nov 8 - Nov 9
Total with taxes and fees
The Bungalow, Pool, Dock, Kayaks, & Game Room
A covered patio with a wooden ceiling, a table with chairs, and a view of a backyard with a grill and greenery.

15. Golf cart included! 5 blocks to the beach, and in historic district!

Golf cart included! 5 blocks to the beach, and in historic district!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (17 reviews)
"The home was perfectly situated in Cape Charles and on a quiet street. The home was well equipped with everything, the kitchen was well stocked with all the cooking pots/pans and anything you needed to cook with. Check out was a breeze! The screened in porch was perfect in the evening. Golf cart is always a nice touch for properties in Cape Charles."
United States
Lori G.
$426 nightly
The price is $482
Nov 9 - Nov 10
Total with taxes and fees
Golf cart included! 5 blocks to the beach, and in historic district!
Private kitchen

16. Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!

Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!
Historic Downtown Cape Charles
$308 nightly
The price is $350
Nov 12 - Nov 13
Total with taxes and fees
Mason Ave Beach Cottage ~ Fire Pit + Outdoor Shower!
A room with a dining table, chairs, a lamp, and a window with blinds.

17. Salt Box, One Block to the Beach

Salt Box, One Block to the Beach
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (24 reviews)
"Loved our stay at the Salt Box! Great location and cute house - wish we could have stayed longer. "
United States
Katie I.
$384 nightly
The price is $414
Nov 10 - Nov 11
Total with taxes and fees
Salt Box, One Block to the Beach
A dining area with a long table, chairs, a candle centerpiece, and a staircase with a railing.

18. Walk to Dining, Beach & Park~Family Friendly Home!

Walk to Dining, Beach & Park~Family Friendly Home!
Historic Downtown Cape Charles
10.0 out of 10, Exceptional, (9 reviews)
"The close proximity to the park was perfect for our children and walking our dog"
United States
Jeff
$278 nightly
The price is $317
Nov 11 - Nov 12
Total with taxes and fees
Walk to Dining, Beach & Park~Family Friendly Home!
A spacious living area with a wooden floor, a sofa, a coffee table, and a staircase.

19. A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!

A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!
Historic Downtown Cape Charles
9.6 out of 10, Exceptional, (15 reviews)
"Really enjoyed our stay! Great location by the park, lots of space for our family. Fun board games, too :)"
United States
Alexa Q.
$536 nightly
The price is $606
Nov 9 - Nov 10
Total with taxes and fees
A Perfect Location Next to Park and Walkable to Town and Beach. Pet Friendly!
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

A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.
Hampton Inn Gloucester

Hampton Inn Gloucester

Hampton Inn Gloucester
Gloucester

10/10 Excellent

Fantastic
United States
Joseph
Reviewed July 31, 2025
Hampton Inn Gloucester

Find out more about Port Haywood

Everything you need to know about Port Haywood 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 Port Haywood 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 Port Haywood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Port Haywood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Port Haywood 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 $33 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 Port Haywood rentals

At Expedia, we put the best Port Haywood 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 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 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 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 vacation rentals in Port Haywood?

Yes, we have vacation rentals near the most popular local attractions in Port Haywood, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Port Haywood has to offer?

The Crows Nest.
Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!: This vacation home rental near Port Haywood is located on the waterfront and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

How many vacation rentals are there in Port Haywood?

Choose from 7 Expedia vacation rentals in Port Haywood for a memorable vacation.

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 larger area, you’ll find Bethel Beach Natural Area Preserve and Bethel Beach.

What are vacation rentals like in Port Haywood?

Vacation rentals are privately owned properties you can book for a short or long stay in Port Haywood. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

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