Gwynn Vacation Rentals

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Gwynn

Property grounds
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (210)
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (302)
"We had a very enjoyable stay. Peaceful, quiet, tranquil. Thoroughly enjoyed it. Met with longtime friends for a getaway. The place isn't fancy, but we weren't looking for fancy, just a quiet hideout. Would stay again."
Cottage on a Private Island in the York River
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (242)
"Excellent base for exploring Williamsburg, Yorktown and Jamestown. Beautiful historic cottage on expansive grounds. Dead quiet."
Historic Cottage on Ware River Estate
Fridge, microwave, oven, stovetop
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (62)
"Seriously, don't think twice about booking this property! It's in a beautiful, quiet setting and about an hour drive from countless attractions. We went to Williamsburg, short 45 minute drive through beautiful country. The property is exceptional! The host has thought of literally everything and well appointed. Looking forward to returning soon!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (111)
"Beautiful home. Very well equipped."
Private, 7-acre waterfront retreat on Winter Harbor Haven
Fridge, microwave, oven, stovetop
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (11)
"Thank you so much for sharing this rental. My family loved being on the water and all were just overwhelmed by the rental. All have rented VRBOs before and all remarked how clean. Also appreciated the good basket, area information and check-out list. As the relative who rented the property, the owners were very responsive to my questions. I'll rent again for family."
The price is $150
$315 total
includes taxes & fees
May 20 - May 21
Welcome to this Waterfront Home with Amazing Views
Property grounds
Peaceful Waterfront Cottage on VA’s Northern Neck
10.0 out of 10, Exceptional, (87)
"We loved our stay at Fred’s property. Unfortunately the weather didn’t cooperate enough for us to enjoy the water, but the views and cozy cottage provided a relaxing time away nonetheless. Location was great — off the beaten path but still a quick drive to town."
Peaceful Waterfront Cottage on VA’s Northern Neck
Fridge, microwave, stovetop, dishwasher
Waterfront Topping Vacation Home w/ Boat Dock!
10.0 out of 10, Exceptional, (5)
"Very much enjoyed our stay!! Great views and great location. Don’t forget to play ping pong in the garage!"
Waterfront Topping Vacation Home w/ Boat Dock!
Interior
Amazing views of the Chesapeake Bay.
10.0 out of 10, Exceptional, (10)
"We were in town for a reunion with good friends and former neighbors. This cottage was perfect for our needs! Spacious and comfortable. Kitchen stocked with everything you might need. Great view of the river and a covered front porch to sit and enjoy it! Lovely area to walk around as well. Host very responsive! I would definitely stay here again. Highly recommend!"
Amazing views of the Chesapeake Bay.
Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, (31)
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
Beach
Sunflower Cottage - Waterfront; Outdoor shower!
10.0 out of 10, Exceptional, (2)
"The dock and view were spectacular!! The bathroom shower was tiny. We aren’t big, but a full size man would have had issues."
Sunflower Cottage - Waterfront; Outdoor shower!
Sun loungers, beach towels
Walk to Town. 1st floor King Bed & Walk in Shower! Charming Remodel. Fire Pit🔥!
10.0 out of 10, Exceptional, (21)
"We had a nice, comfortable stay in Mathews. Our daughter graduated from USCG BM A School in Yorktown, about 35min from this property. She stayed one night with us, along with my husband, my father in law, two teens and two dogs. The house is very dog friendly with supplies and a big yard. Clean, comfortable place to hang out! Awesome communication with host! Great breakfast at Howard-Dooley Cafe just a few minutes away."
The price is $125
$277 total
includes taxes & fees
May 21 - May 22
Walk to Town. 1st floor King Bed & Walk in Shower! Charming Remodel. Fire Pit🔥!
Fridge, microwave, oven, stovetop
River Vibes@ the Piankatank River
10.0 out of 10, Exceptional, (14)
"The owner was very responsive in communicating before & during our trip. The property is very well kept & clean. He had everything that we needed for our long weekend. The backyard offers an awesome retreat from city life. We are planning to return in the future. Very pleased with everything that they had to offer. Owner was super nice."
River Vibes@ the Piankatank River
Property grounds
Water front Oasis with pickle-ball court and hot tub
10.0 out of 10, Exceptional, (1)
"Had a great experience staying at the property. It was as clean and well maintained. The host Jessica was a delight to work with."
The price is $1,376
$2,325 total
includes taxes & fees
Jun 8 - Jun 9
Water front Oasis with pickle-ball court and hot tub
3 bedrooms, iron/ironing board, WiFi, bed sheets
Vacation Getaway on Chesapeake Bay
10.0 out of 10, Exceptional, (138)
"The house is always immaculate and the amenities are great. The host is the best. The location can't be beat."
Vacation Getaway on Chesapeake Bay
Property grounds
Have you made your summer vacay plans yet at the Rivah in Irvington?
10.0 out of 10, Exceptional, (264)
"Classic Northern Neck cottage beautifully maintained and wonderfully comfortable."
Have you made your summer vacay plans yet at the Rivah in Irvington?
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (38)
"Everything you want to do is right there at the house..Fishing, crabbing. Canoeing, kayaking and so much more. Already planning a trip back this summer."
Enjoy family fun and Sunsets at Piankatank Point.
Property grounds
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (28)
"Inside decor was spot on. Kitchen was well-stocked, and we enjoyed the dock and fishing. Host was a great communicator."
The Little Blue Cottage - Topping : Waterfront!
TV, fireplace, DVD player, books
Riverfront Cottage: Fire Pit & Kayaks
9.8 out of 10, Exceptional, (25)
"It was beautiful. We loved wake up to the beautiful water everyday."
Riverfront Cottage: Fire Pit & Kayaks
Don't see what you're looking for?
See all available properties in Gwynn
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.

Other types of properties in Gwynn you may be interested in

Property grounds
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (210)
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Exterior
Holiday Inn Express Gloucester, an IHG Hotel
3.5 star property
7.2 out of 10, Good, (508)
"The room was a good size very spacious. I did find dirty linen in the bathroom. And the ac was crazy. It makes a weird sound off and on then cuts off "
The price is $110
$122 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express Gloucester, an IHG Hotel
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.

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

Gwynn vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gwynn. 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 Gwynn 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 $125 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 Gwynn rentals

At Expedia, we put the best Gwynn 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 Gwynn 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 Gwynn 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 Gwynn. 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

Can I find vacation rentals in Gwynn?

Yes, we give you a choice of vacation rentals near the most popular sights in Gwynn, or you can select a more secluded option if you want a relaxing place to stay. Gwynn is known for its museums.

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

Private 5-acre Waterfront Peninsula with Beach: This vacation home rental near Gwynn is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Gwynn?

Choose from 13 Expedia vacation rentals in Gwynn for a memorable vacation.

What can I see and do in Gwynn?

Explore the area and family-friendly sights such as Deltaville Maritime Museum, or get out into nature at a spot like White Stone Beach. In the larger area, you’ll find Gwynn's Island Musuem and Deltaville Marina.

What are vacation rentals like in Gwynn?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Gwynn. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.

Recent reviews of Gwynn properties
Expedia verified reviews

Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.

Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.

5/5 Excellent
Can't wait to return!
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
A verified traveler from Salem stayed at Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Posted 5 days ago
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.