Gwynn Holiday Rentals

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Holiday Rentals in Gwynn

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Grimstead
10.0 out of 10, Exceptional, (219)
"Everything you need is here, crab pots-caught a few blue crabs. Went fishing, we caught skate, croaker and an eel. 3 Kayaks, beach chairs, SUP , well stockedgrill, etc. "
United States
Kris K.
Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Gwynn's Island
10.0 out of 10, Exceptional, (35)
"We have enjoyed 2 stays at the cottage. It is a wonderful location and the owners have been great and are very thoughtful. The beach is perfect, and we love the neighborhood. We can't wait to visit again!"
United States
karen w.
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Cottage on a Private Island in the York River

Gloucester Point
10.0 out of 10, Exceptional, (357)
"We had a terrific vacation at a lovely home in a unique location. "
United States
Benjamin E.
Cottage on a Private Island in the York River

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Diggs
The price is NZ$68
includes taxes & fees
1 Dec - 2 Dec
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

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

Irvington
9.6 out of 10, Exceptional, (172)
"We enjoyed our stay so close to the Tides Inn for the Taste of the Bay. Irvington is a quaint walkable town, perfect for getting away from the hustle and bustle of fast paced locations."
United States
Chris O.
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Hallieford
10.0 out of 10, Exceptional, (157)
"Peaceful setting wonderful views. Location is wonderful. Excellent!"
United States
Michael B.
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

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

Hayes
9.4 out of 10, Exceptional, (130)
"Beautiful property! Very spacious with an amazing view! Clean, in a great location, friendly neighbors! "
United States
Heather E.
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

Bay Dream Believer Cottage on Beautiful East River Waterfront

2.0 star property
Mathews
10.0 out of 10, Exceptional, (22)
"Great location. Quite,clean, relaxing "
United States
Randy C.
The price is NZ$816
includes taxes & fees
10 Nov - 11 Nov
Bay Dream Believer Cottage on Beautiful East River Waterfront

Spacious waterfront home with dock and sunset view

Kilmarnock
9.6 out of 10, Exceptional, (12)
"We were attending a family reunion. Great to wake up and look out to see the water. So relaxing and serene. Just enough space to relax and unwind. I would however suggest to the owner to put some railings on the patio. We had a few seniors who need that extra support when stepping up. The grands loved fishing from the pier."
United States
Sneatha L.
Spacious waterfront home with dock and sunset view

The Little Blue Cottage - Topping : Waterfront!

Topping
9.8 out of 10, Exceptional, (50)
"Lovely place and attentive owner, felt right at home and will definitely return to this property for future trips to the area."
United States
Lory H.
The Little Blue Cottage - Topping : Waterfront!

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Gloucester
10.0 out of 10, Exceptional, (175)
"Clean and well appointed cottage with beautiful views. The owners gave great recommendations for local spots to eat and have fun. Really enjoyed the stay. "
United States
Makayla L.
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

The Farm Overlook Treehouse At Blanchard Farm

Diggs
10.0 out of 10, Exceptional, (1)
The price is NZ$205
includes taxes & fees
10 Nov - 11 Nov
The Farm Overlook Treehouse At Blanchard Farm

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

Hayes
8.0 out of 10, Very good, (4)
"Erik was a great host. His dog hosted too:) it felt like home. We were in town for a celebration of life and the house helped us stay happy during sad time."
United States
Roxanne C.
The price is NZ$2,481
includes taxes & fees
8 Dec - 9 Dec
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

Irvington
10.0 out of 10, Exceptional, (303)
"Excellent property"
United States
Brock S.
Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

Bubba Butler's Cottage

Locust Hill
10.0 out of 10, Exceptional, (21)
"We had a fantastic stay. I could not have asked for better view of the river, and both sunsets and sunrises were perfect. It was a perfect place to unwind reading and writing. "
United States
Amy B.
Bubba Butler's Cottage

Nassawadox Creek Waterfront Home with Private Pool

Exmore
10.0 out of 10, Exceptional, (60)
"Beautiful setting. House has everything we needed. Plenty of room for us. Peaceful. Thank you."
United States
Sherry G.
Nassawadox Creek Waterfront Home with Private Pool

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

Hudgins
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay at this property! The location was perfect- beautiful and peaceful right on the water. Dock was a great place to hang out at same with the cut-out beach areas. There is a great little restaurant nearby called hole-in-the-wall which had great food and the marina is just minutes away if you are looking to rent a boat or get out on the water.Overall, it was a fantastic stay and I would definitely recommend this home to anyone looking for a relaxing getaway in a quiet...
United States
Hoda P.
The price is NZ$726
includes taxes & fees
24 Nov - 25 Nov
Bayfront Escape, Private Dock, Large Deck, and Views!

Serenity on the Rappahannock

White Stone
10.0 out of 10, Exceptional, (9)
"Clean; Beautiful views;Good bedroom to bathroom ratio;Well-appointed kitchen;Great water access;Quiet location;Easy check-in;Excellent communication with host."
United States
Carl H.
Serenity on the Rappahannock

Beach House on Chesapeake Bay!

Hudgins
10.0 out of 10, Exceptional, (134)
"The property was better than advertised. It was beautiful, clean, very well-appointed, and serene. We wanted for nothing and we loved every minute. This is a lovely location for a quiet getaway and we would happily do it again."
United States
Eric J.
Beach House on Chesapeake Bay!

Private, 7-acre waterfront retreat on Winter Harbor Haven

Port Haywood
10.0 out of 10, Exceptional, (141)
"We loved this secluded quiet property, especially the screened in porch. The house was clean and comfortable. We caught and ate fresh blue crab off the dock ,enjoyed day trips to Williamsburg and Norfolk, and spent time at the local Haven Beach."
United States
Kyle K.
Private, 7-acre waterfront retreat on Winter Harbor Haven
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

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$68 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?

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES! : This holiday home rental outside of Gwynn is located on the beach, 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 balcony, 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 8 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 Chesapeake Bay. 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.