Gwynn Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Gwynn Vacation Homes

Retreat to Fairytale Cottage with Pool, Kayak
Terrace/patio

Retreat to Fairytale Cottage with Pool, Kayak

10.0 out of 10, Exceptional, (11)
"It was fairytale cottage ! "
Retreat to Fairytale Cottage with Pool, Kayak
Private Beach & Deck: Bayfront Home in Hayes!
Fridge, microwave, stovetop, dishwasher

Private Beach & Deck: Bayfront Home in Hayes!

10.0 out of 10, Exceptional, (26)
"Enjoyed the property "
Private Beach & Deck: Bayfront Home in Hayes!
Pet-Friendly Gem w/ Private Dock in Deltaville!
TV, DVD player, books, stereo

Pet-Friendly Gem w/ Private Dock in Deltaville!

8.8 out of 10, Excellent, (9)
"Wonderful place for four artists in 5-day plein air event. Great location, views of river, sunrise and sunsets. Quiet, private, comfortable. "
Pet-Friendly Gem w/ Private Dock in Deltaville!
'Pop Castle' Historic Gem on the Rappahannock River
Interior

'Pop Castle' Historic Gem on the Rappahannock River

10.0 out of 10, Exceptional, (97)
"Another wonderful week at Pop Castle! Can’t wait to be back!"
'Pop Castle' Historic Gem on the Rappahannock River
Private, 7-acre waterfront retreat on Winter Harbor Haven
Property grounds

Private, 7-acre waterfront retreat on Winter Harbor Haven

10.0 out of 10, Exceptional, (136)
"The property is extremely comfortable and equipped with absolutely everything one might need. A wonderful getaway!"
Private, 7-acre waterfront retreat on Winter Harbor Haven
River Beachfront- Spacious Dog & Family Friendly 3 Bedroom Home on Shared Beach
Exterior

River Beachfront- Spacious Dog & Family Friendly 3 Bedroom Home on Shared Beach

9.6 out of 10, Exceptional, (54)
"The stay is great, the house is spacious with a beautiful view. "
River Beachfront- Spacious Dog & Family Friendly 3 Bedroom Home on Shared Beach
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Dining

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

10.0 out of 10, Exceptional, (10)
"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!
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Beach

Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>

9.6 out of 10, Exceptional, (135)
"This is a roomy well-equipped home with fun and interesting decor. It is conveniently located in a very nice neighborhood near restaurants, shopping and entertainment. The check-in and check-out were seamless. The owner quickly responded to all inquiries. "
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Spacious waterfront home with dock and sunset view
Outdoor dining

Spacious waterfront home with dock and sunset view

9.4 out of 10, Exceptional, (6)
Spacious waterfront home with dock and sunset view
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (124)
"Great location for a weekend spent at Jamestown, Colonial Williamsburg and Busch Gardens! Awesome that we got to use the canoe! Also, really nice kitchen!"
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (51)
"We had everything we needed. A very quiet, relaxing weekend. "
Nassawadox Creek Waterfront Home with Private Pool
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!
Property grounds

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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!
Little Bay Waterfront Retreat
Interior

Little Bay Waterfront Retreat

9.8 out of 10, Exceptional, (62)
"Quiet and peaceful! Just what we needed to unwind from everyday stress! Wish the weather had cooperated more! Property Manager (Vickie) always got right back to us and that is appreciated!"
Little Bay Waterfront Retreat
Waterfront Hartfield Vacation Rental w/ Dock!
Terrace/patio

Waterfront Hartfield Vacation Rental w/ Dock!

9.8 out of 10, Exceptional, (26)
"Great place"
Waterfront Hartfield Vacation Rental w/ Dock!
Charming Waterfront Home on Sought After Piankatank!
Property grounds

Charming Waterfront Home on Sought After Piankatank!

10.0 out of 10, Exceptional, (52)
"I cannot say enough about this property. The kitchen is very well stocked, everything was very clean. Very quiet neighborhood. The sunrises and the sunsets were unbeatable from the dock! This is a beautiful place to go, disconnect and enjoy peace. The area is also very rich in history, and there is lots to explore! We will definitely visit again in warmer months. "
Charming Waterfront Home on Sought After Piankatank!
Coco’s Cabana
Fridge, microwave, oven, stovetop

Coco’s Cabana

9.6 out of 10, Exceptional, (30)
"Great "
Coco’s Cabana
The Deadrise Inn, Sleeps12, Spacious, Newly Renovated
Fridge, microwave, oven, stovetop

The Deadrise Inn, Sleeps12, Spacious, Newly Renovated

9.8 out of 10, Exceptional, (14)
"Beautiful prpoerty with plenty of space. The fenced in backyard is awesome. Resaurants within walking distance."
The Deadrise Inn, Sleeps12, Spacious, Newly Renovated
RivahMojo on Mill Creek-just off RappahannockRiver
Exterior

RivahMojo on Mill Creek-just off RappahannockRiver

10.0 out of 10, Exceptional, (17)
"Nice location, very clean and well-stocked with most anything one could need."
The price is CA $292
CA $618 total
includes taxes & fees
Aug 17 - Aug 18
RivahMojo on Mill Creek-just off RappahannockRiver
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (5)
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!
Fridge, microwave, oven, stovetop

Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!

10.0 out of 10, Exceptional, (187)
"Family came up to visit us from Texas. Everyone enjoyed the sights and new memories made. Plenty space and weather was fantastic. "
Spectacular Riverfront Retreat with Kid-Friendly Beach. Enjoy the ‘Riva Life’!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gwynn Hotel Reviews

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

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

10/10 Excellent
"From start to finish, Cheri made this an easy process. She is very helpful and responds quickly. What you see is what you get. The listing is 100% accurate. The cottage is quaint and cozy. Cheri is very organized and had everything we needed for our stay. We enjoyed catching crabs, fishing from the beach, kayaking and mastering the paddle board. We took a charter out on the Chesapeake bay to catch Spanish Mackerel. The neighbor to the left was outside once and was very friendly. Otherwise, we really didn't see many people. There are stores and quaint restaurants near by. I could not have been happier. If you are looking for a place to relax, this cottage is for you. "
Tina W. 7-night trip
Posted 2 days ago
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water