Gwynn Vacation Rentals

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Vacation Rentals in Gwynn

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

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
On the beach, sun loungers
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

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

Gwynn's Island
10.0 out of 10, Exceptional, (35)
"Great location Great beachGreat homeGreat Neighbors"
United States
Anthony C.
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
Exterior
Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

Gloucester Point
10.0 out of 10, Exceptional, (358)
"Great location, great accommodations! "
United States
Ivan R.
Cottage on a Private Island in the York River
Outdoor dining
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Diggs
$35 nightly
The price is $39
Dec 1 - Dec 2
Total with taxes and fees
RV Site On Blanchard Farm -MAX RV LENGTH 24 FT
Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool

Exmore
10.0 out of 10, Exceptional, (60)
"Very nice experience "
United States
Chris C.
Nassawadox Creek Waterfront Home with Private Pool
Fridge, microwave, oven, stovetop
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

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
Property grounds
The Little Blue Cottage - Topping : Waterfront!

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!
Fridge, microwave, oven, stovetop
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

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.
Terrace/patio
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Cobbs Creek
9.6 out of 10, Exceptional, (13)
"The place and grounds were beautiful. The hosts were extraordinarily accommodating."
United States
Janet C.
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE
Outdoor dining
Spacious waterfront home with dock and sunset view

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
Exterior
Mid-century modern meets classic cape on the coast.

Mid-century modern meets classic cape on the coast.

Moon
9.8 out of 10, Exceptional, (18)
"We enjoyed our stay at this house. Rebecca, the host, ensures you have all the amenities needed while staying there. The home was clean and welcoming. We enjoyed the walk down to the dock each day we were there. It was quiet and peaceful waterfront community. We really enjoyed our stay!"
United States
Julie S.
Mid-century modern meets classic cape on the coast.
Exterior
Bay Dream Believer Cottage on Beautiful East River Waterfront

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.
$421 nightly
The price is $464
Nov 18 - Nov 19
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
3 bedrooms, memory foam beds, iron/ironing board, free WiFi
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

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

Hallieford
10.0 out of 10, Exceptional, (157)
"Charming cottage in a quiet neighborhood. Waterfront and views across the Bay are amazing. My third trip there in past few years."
United States
Marsha H.
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Exterior
The Farm Overlook Treehouse At Blanchard Farm

The Farm Overlook Treehouse At Blanchard Farm

Diggs
10.0 out of 10, Exceptional, (1)
$105 nightly
The price is $116
Nov 18 - Nov 19
Total with taxes and fees
The Farm Overlook Treehouse At Blanchard Farm
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.

Enjoy family fun and Sunsets at Piankatank Point.

Saluda
9.6 out of 10, Exceptional, (67)
"This is our second time with this rental and it is amazing. The best laid back area and very responsive hosts. "
United States
Elisa G.
Enjoy family fun and Sunsets at Piankatank Point.
Property grounds
Bubba Butler's Cottage

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
Interior
Little Bay Waterfront Retreat

Little Bay Waterfront Retreat

White Stone
9.8 out of 10, Exceptional, (67)
"Great location! Everything was clean; house had everything we needed and more. Wonderful to have private beach area"
United States
Tim N.
Little Bay Waterfront Retreat
Outdoor dining
Autumn in Irvington - it’s so inviting and gorgeous. And it’s waiting for you!

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!
Terrace/patio
Bayfront Escape, Private Dock, Large Deck, and Views!

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.
$358 nightly
The price is $395
Dec 1 - Dec 2
Total with taxes and fees
Bayfront Escape, Private Dock, Large Deck, and Views!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven

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

Hampton Inn Gloucester

Hampton Inn Gloucester

10/10 Excellent
"Very quiet at night! Beds were comfortable"
Kathy 2-night trip
Posted 3 days ago
Hampton Inn Gloucester

Find out more about Gwynn

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 $39 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.

Explore a world of travel with Expedia

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?

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES! : Located near Gwynn, this vacation home rental is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Gwynn?

Choose from 8 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 Chesapeake Bay. 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.