Gwynn Holiday Rentals

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Holiday Rentals in Gwynn

Our top choices for Gwynn holiday rentals

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

10.0 out of 10, Exceptional, (217)
"We had a great time staying here. The private beach was exactly what we needed to relax and have fun. "
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

The Little Blue Cottage - Topping : Waterfront!

9.8 out of 10, Exceptional, (46)
"The house was so amazing! The owners are very responsive and helpful. The house was so clean and loved the personal touches. We will be back!"
The Little Blue Cottage - Topping : Waterfront!

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

9.6 out of 10, Exceptional, (168)
"We throughly enjoyed our time at the little blue house! We would definitely stay here again."
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (351)
"We would definitely stay here again!"
Cottage on a Private Island in the York River

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (57)
"Beautiful property and house. Everything was very clean. Great neighbors who helped us out in a pinch. And Nancy, our host, so kind and gracious. I hope to come back many more times."
Nassawadox Creek Waterfront Home with Private Pool

Bay Dream Believer Cottage on Beautiful East River Waterfront

2.0 star property
10.0 out of 10, Exceptional, (22)
"Wonderful location, host communicated well"
The price is NZ$772
includes taxes & fees
24 Sept - 25 Sept
Bay Dream Believer Cottage on Beautiful East River Waterfront

Enjoy family fun and Sunsets at Piankatank Point.

9.6 out of 10, Exceptional, (66)
"Property is awesome. Just as advertised. Tons of space for families and kids and excellent fishing off the dock. Would absolutely stay here again"
Enjoy family fun and Sunsets at Piankatank Point.

Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!

10.0 out of 10, Exceptional, (11)
"Nice, clean place with thoughtful touches, plenty of space, and amazing grounds. The owner was kind enough to let the kids meet the new puppies. Definitely would stay again stay "
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!

Spacious waterfront home with dock and sunset view

9.4 out of 10, Exceptional, (8)
"This spot was perfect for our gathering of family members from Colorado and Maryland for a few sweet days together. The sunrises and sunsets and water birds hit all the buttons for grandma. The proximity to water with toys and similarly aged kids next door couldn’t have been more perfect. The house was very well equipped, and stocked with perfect items to complete our preparation, or lack thereof. We had solitude from the rest of the world to reconnect and enjoy each other fully in a beautiful...
Spacious waterfront home with dock and sunset view

Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

9.4 out of 10, Exceptional, (127)
"We had a great time. The place was as expected. Clean and comfortable and very spacious. "
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!

2.0 star property
10.0 out of 10, Exceptional, (8)
"We thoroughly enjoyed our weekend. The house was lovely and clean, and the lawn and dock were perfect for getting some sun and watching the ospreys tend their nest. Aaron greeted us and made us feel welcome and responded to the one or two questions we had during our stay. "
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

10.0 out of 10, Exceptional, (8)
"Great place, very nice hosts beautiful location "
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

9.6 out of 10, Exceptional, (12)
"This is a lovely quiet property on the water. It was the best supplied property I’ve ever stayed in with food in the cupboard and fridge and bath room toiletries, even an extra toothbrush. (Good thing because I forgot mine.) There’s plenty of room to spread out and even a pool table. Highly recommended for your next trip to this wonderful little corner of the world. "
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Little Bay Waterfront Retreat

9.8 out of 10, Exceptional, (66)
"Enjoyed our getaway at this bayfront property in a very quiet and private neighborhood. White sandy beach in a protected bay. Water was calm and you could safely walk out quite far. Very nice sunroom for morning sunrises. "
Little Bay Waterfront Retreat

Water front Oasis with pickle-ball court and hot tub

9.0 out of 10, Wonderful, (8)
"The Cradle Point Estate is absolutely amazing. Family-Friendly and great location for a retreat. Peace and Serenity The hosts are phenomenal. Will rent again in the very near future In The Spirit Of Community"
Water front Oasis with pickle-ball court and hot tub

Bayfront Escape, Private Dock, Large Deck, and Views!

10.0 out of 10, Exceptional, (1)
"This house has beautiful views and it was only about 45 min to Williamsburg. It is on Hills Bay, which flows into the Chesapeake Bay. The water is very shallow and would be great for younger kids. We brought kayaks and enjoyed our time on the water. It would be fantastic for someone that owns a boat too. The water doesn’t have many waves, but we tied a party size float to part of the dock and all the kids, ages 10-19, loved our time there. Since I’m the first review, I think I might be the first...
Bayfront Escape, Private Dock, Large Deck, and Views!

Perfect for long-term workers & short stays—comfort, style & convenience await!

8.4 out of 10, Very good, (16)
"Was very warm and inviting atmosphere. Easy to find and off the main traffic at the same time very convenient. "
Perfect for long-term workers & short stays—comfort, style & convenience await!

Charming 2-bedroom house on the Chesapeake Bay

9.4 out of 10, Exceptional, (13)
"Property was very nice and has a lot history with it. "
Charming 2-bedroom house on the Chesapeake Bay

The Farm Overlook Treehouse At Blanchard Farm

10.0 out of 10, Exceptional, (1)
The price is NZ$160
includes taxes & fees
24 Sept - 25 Sept
The Farm Overlook Treehouse At Blanchard Farm

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (49)
"Easy access to the property and to town. Very quite and comfy."
Cozy cottage on the Chesapeake Bay
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 Gwynn Hotel Reviews

Find out more about Gwynn

Find out more about Gwynn

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

Gwynn holiday 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 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 Gwynn 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 Gwynn holiday rentals we have selected for you start as low as NZ$160 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gwynn rentals

At Expedia, we put the best Gwynn 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 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 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 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 holiday rentals in Gwynn?

Yes, there are holiday rentals close to the most popular sights in Gwynn, or you can select a more secluded option if you're looking for a relaxing stay. Gwynn is known for its museums.

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

Nassawadox Creek Waterfront Home with Private Pool: This holiday home rental outside of Gwynn is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Gwynn?

Choose from 7 Expedia holiday rentals in Gwynn for a memorable holiday.

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 Holly Point Nature Park. In the wider area, you’ll find Gwynn's Island Musuem and Deltaville Marina.

What are holiday rentals like in Gwynn?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gwynn. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks 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 choice for a family getaway.