Gwynn Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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.
The price is AED 323
AED 1,450 total
includes taxes & fees
23 Nov - 24 Nov
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.
The price is AED 495
AED 1,035 total
includes taxes & fees
8 Nov - 9 Nov
Deltaville 2BR Retreat, Walk to Museum, Boat Parking
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

3. Campsite #4 At Blanchard Farm

Campsite #4 At Blanchard Farm
Diggs
The price is AED 66
AED 122 total
includes taxes & fees
8 Nov - 9 Nov
Campsite #4 At Blanchard Farm
A modern kitchen with white cabinets, stainless steel appliances, a double sink, and a large window.

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.
The price is AED 428
AED 1,182 total
includes taxes & fees
16 Nov - 17 Nov
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town
A forest trail with a clear path, surrounded by tall trees and dense underbrush.

5. Campsite #3 At Blanchard Farm

Campsite #3 At Blanchard Farm
Diggs
The price is AED 66
AED 122 total
includes taxes & fees
8 Nov - 9 Nov
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.
The price is AED 367
AED 1,029 total
includes taxes & fees
9 Nov - 10 Nov
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
The price is AED 463
AED 1,271 total
includes taxes & fees
8 Nov - 9 Nov
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.
The price is AED 907
AED 1,669 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is AED 393
AED 666 total
includes taxes & fees
8 Nov - 9 Nov
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
The price is AED 617
AED 1,224 total
includes taxes & fees
8 Nov - 9 Nov
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.
The price is AED 566
AED 1,365 total
includes taxes & fees
16 Nov - 17 Nov
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
The price is AED 643
AED 1,681 total
includes taxes & fees
8 Nov - 9 Nov
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.
The price is AED 485
AED 1,280 total
includes taxes & fees
8 Nov - 9 Nov
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
The price is AED 621
AED 1,316 total
includes taxes & fees
8 Nov - 9 Nov
Radiant Gloucester House w/ Private Porch!
A room with wicker furniture, a large mirror, and framed pictures on the wall.

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.
The price is AED 984
AED 1,888 total
includes taxes & fees
8 Nov - 9 Nov
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.
The price is AED 579
AED 1,551 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is AED 698
AED 1,173 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is AED 661
AED 1,578 total
includes taxes & fees
1 Dec - 2 Dec
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.
The price is AED 1,153
AED 1,978 total
includes taxes & fees
9 Nov - 10 Nov
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

A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.
Hampton Inn Gloucester

Hampton Inn Gloucester

Hampton Inn Gloucester
Gloucester

10/10 Excellent

Fantastic
United States
Joseph
Reviewed July 31, 2025
Hampton Inn Gloucester

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.