A pier extending into calm waters at sunset with a clear sky.

Gwynn Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Gwynn vacation rentals

A spacious living room with a large gray sectional sofa, a wooden coffee table, and a ceiling fan. There are nautical decorations on the wall and a view of a lake through large glass doors.

1. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
9.8 out of 10, Exceptional, (52 reviews)
"This place was a perfect getaway. Quiet and a beautiful view!"
United States
David P.
$348 nightly
The price is $384
Nov 23 - Nov 24
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A small, single-story house with a porch, a wooden deck, and a brick pathway.

2. Deltaville 2BR Retreat, Walk to Museum, Boat Parking

Deltaville 2BR Retreat, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was perfect - loved staying here. "
United States
John L.
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A hammock tied between two trees in a forested area.

3. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 19 - Nov 20
Total with taxes and fees
Campsite #4 At Blanchard Farm
A sandy beach path leading to the ocean, surrounded by dry grass.

4. 1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
Mathews
10.0 out of 10, Exceptional, (43 reviews)
"We had a great time at Baydreamin'."
United States
Crystal D.
$277 nightly
The price is $306
Nov 16 - Nov 17
Total with taxes and fees
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
A hammock tied between two trees in a forested area.

5. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
$30 nightly
The price is $33
Nov 10 - Nov 11
Total with taxes and fees
Campsite #3 At Blanchard Farm
A bedroom with a bed, bedside tables, a window with curtains, a patterned rug, and a ceiling vent.

6. Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (42 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
$236 nightly
The price is $272
Nov 10 - Nov 11
Total with taxes and fees
Belle Haven - High Speed internet, walk to town
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

7. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (35 reviews)
"We loved the 1920’s feeling to the home. The cleanliness and quiet location were exactly what we were looking for. We were just a block from the historical center and took advantage of the shops and eateries. We would definitely stay here afain"
United States
David
$303 nightly
The price is $337
Nov 10 - Nov 11
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A front door with a wreath, a wooden porch, and a gravel pathway.

8. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront
Mathews
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful location, host communicated well"
United States
Nicole K.
$400 nightly
The price is $441
Nov 10 - Nov 11
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
A wooden dock with chairs facing a calm lake, surrounded by dense forest.

9. Private home on creek with dock.

Private home on creek with dock.
Lancaster
9.2 out of 10, Wonderful, (15 reviews)
"Great place loved it!"
United States
Brandon W.
$163 nightly
The price is $175
Nov 10 - Nov 11
Total with taxes and fees
Private home on creek with dock.
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

10. The Bungalow, Pool, Dock, Kayaks, & Game Room

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
$295 nightly
The price is $325
Nov 10 - Nov 11
Total with taxes and fees
The Bungalow, Pool, Dock, Kayaks, & Game Room
A modern kitchen with a central island, stainless steel appliances, and teal bar stools.

11. Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Kilmarnock
10.0 out of 10, Exceptional, (7 reviews)
"Nice rambler in a great in town location with hot tub, firepit, and fenced in yard. Also great value for the price. "
United States
Melinda H.
$332 nightly
The price is $376
Nov 17 - Nov 18
Total with taxes and fees
Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
A porch with two rocking chairs, a black door, and a mailbox.

12. The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (9 reviews)
"This home is comfortable, well appointed, and in a great location. Host is accommodating and communicates appropriately I highly recommend this property!"
United States
Anonymous traveler
$393 nightly
The price is $445
Nov 11 - Nov 12
Total with taxes and fees
The Nook in Kilmarnock Va 3 bedroom
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

13. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Restored 1930s Cottage on 1 Acre w/ Fire Pit
Hayes
9.6 out of 10, Exceptional, (97 reviews)
"Our family of 6 (age range 20’s to 80’s) enjoyed all of the rooms and porches. The air conditioners kept the home comfortable and the porches were cozy for those who like it warmer. We liked the convenience of being able to make our own breakfasts and dinners here. Having a grill was a bonus."
United States
Susan C.
$305 nightly
The price is $339
Nov 10 - Nov 11
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A kitchen with dark blue cabinets, a gas stove, a sink, and a window overlooking the backyard.

14. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Nov 10 - Nov 11
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A wooden picnic table with a pitcher, glasses, and a plate set on a grassy area by a body of water.

15. Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden

Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
Locust Hill
10.0 out of 10, Exceptional, (41 reviews)
"The hosts made sure that everything in the house made one feel comfortable and at home. The view is fantastic and the landscaping with the rose garden and pool on a sunny day is inviting and relaxing. We enjoyed our stay "
United States
Mary S.
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

16. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.2 out of 10, Wonderful, (27 reviews)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
$352 nightly
The price is $411
Nov 10 - Nov 11
Total with taxes and fees
Smith Beach cottage w/ private sunset
A wooden deck with a chair, a welcome mat, and a view of a forest.

17. The Waverly Tree House

The Waverly Tree House
Machipongo
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and clean spot. Great quiet morning views of the creak. We enjoyed a relaxing stay. It had everything we needed. "
United States
Jeanna C.
$253 nightly
The price is $282
Nov 10 - Nov 11
Total with taxes and fees
The Waverly Tree House
A house surrounded by dense greenery and a small dock extending into a body of water.

18. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (79 reviews)
"We loved our stay. We have stayed here multiple times over the years and our entire family, including the dog look forward to it. Hope to return."
United States
Jayson J.
$375 nightly
The price is $417
Dec 1 - Dec 2
Total with taxes and fees
Nassawadox Creek Waterfront Home with Private Pool
A dining area with a dark wooden table, white chairs, a modern chandelier, and framed artwork on the wall.

19. Waterfront Retreat with Office and Private Dock, Boats!

Waterfront Retreat with Office and Private Dock, Boats!
Weems
9.8 out of 10, Exceptional, (28 reviews)
"Nicely equipped, well stocked, clean and neat. Good location with a canoe and kayaks to get out on the cove. Close drive to the three towns in the area with a number of good lunch/dinner spots. Host was very helpful."
United States
Ron H.
$488 nightly
The price is $524
Nov 10 - Nov 11
Total with taxes and fees
Waterfront Retreat with Office and Private Dock, Boats!
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

Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

10/10 Excellent
"We had a lovely time on the private island- a unique and beautiful place. Enjoyed sunset on one porch and sunrise on another. And very convenient to historical sites, great dining, and fun activities. Hope to return someday."
margaret j. 2-night trip
Posted 8 days ago
Cottage on a Private Island in the York River

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 $339 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?

Gwynn's Island Gem | Private Beach & Bay Views: This highly rated vacation home rental in Gwynn is located on the waterfront and has a patio, a barbecue grill, and air-conditioning 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.

How many vacation rentals are there in Gwynn?

Choose from 9 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 Museum 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.