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

Holiday Homes in Gwynn

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Gwynn holiday homes

A small, single-story house with a red door, a porch with a white railing, and a number '70' sign.

1. Luxury Studio Guesthouse, Walk to Museum, Boat Parking

Luxury Studio Guesthouse, Walk to Museum, Boat Parking
Deltaville
10.0 out of 10, Exceptional, (61 reviews)
"Awesome little place. We absolutely enjoyed staying here. Very clean and had all amenities one would need. Will definitely book again. "
United States
Stan R.
The price is €279
includes taxes & fees
26 Oct - 27 Oct
Luxury Studio Guesthouse, Walk to Museum, Boat Parking
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

2. Nice 3-bedroom house with AC in peaceful Hartfield

Nice 3-bedroom house with AC in peaceful Hartfield
Hartfield
The price is €203
includes taxes & fees
25 Oct - 26 Oct
Nice 3-bedroom house with AC in peaceful Hartfield
A bedroom with a bed, bedside tables, a window with curtains, a patterned rug, and a ceiling vent.

3. 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 €261
includes taxes & fees
25 Oct - 26 Oct
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.

4. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
Gloucester
9.4 out of 10, Exceptional, (34 reviews)
"This is a very comfortable clean home in a nice quiet neighborhood. It’s very close to some excellent restaurants and places of interest. We especially enjoyed the sunroom."
United States
Joseph B.
The price is €323
includes taxes & fees
25 Oct - 26 Oct
Radiant Gloucester House w/ Private Porch!
A dining area with a view of a lake and trees, featuring white tables and benches, ceiling fans, and large windows.

5. RivahMojo on Mill Creek-just off RappahannockRiver

RivahMojo on Mill Creek-just off RappahannockRiver
Topping
10.0 out of 10, Exceptional, (26 reviews)
"Property was lovely, host very responsive, couldn’t ask for more!"
United States
Donna B.
The price is €395
includes taxes & fees
27 Oct - 28 Oct
RivahMojo on Mill Creek-just off RappahannockRiver
A small, single-story house with a porch, a wooden deck, and a brick pathway.

6. 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 modern kitchen with a central island, stainless steel appliances, and teal bar stools.

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

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
Kilmarnock
10.0 out of 10, Exceptional, (6 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 €332
includes taxes & fees
2 Nov - 3 Nov
Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~
A porch with two rocking chairs, a black door, and a mailbox.

8. The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (8 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 traveller
The price is €429
includes taxes & fees
24 Oct - 25 Oct
The Nook in Kilmarnock Va 3 bedroom
A covered outdoor area with a pool, wicker furniture, and large windows offering a view of the outdoors.

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

The Bungalow, Pool, Dock, Kayaks, & Game Room
Topping
The price is €323
includes taxes & fees
24 Oct - 25 Oct
The Bungalow, Pool, Dock, Kayaks, & Game Room
A large house with multiple decks and a view of a lake.

10. 9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater

9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
North
8.6 out of 10, Excellent, (14 reviews)
"The house was perfect for my coworkers and I who were in the area for work for a couple days. Jessica was friendly and communicated well. Would recommend for anyone looking for a lot of space to relax in a quiet area."
United States
Jonas M.
The price is €1,210
includes taxes & fees
29 Oct - 30 Oct
9BR Waterfront Oasis! Pickleball, Hot tub, Sauna & Theater
A wooden dock with chairs facing a calm lake, surrounded by dense forest.

11. 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 €186
includes taxes & fees
15 Nov - 16 Nov
Private home on creek with dock.
A small, single-story house with a porch, a wooden deck, and a brick pathway.

12. Two Private Cottages 3BR, Boat Parking, Walk to Marinas

Two Private Cottages 3BR, Boat Parking, Walk to Marinas
Deltaville
10.0 out of 10, Exceptional, (1 review)
"Clean house, comfy"
United States
Ellen M.
Two Private Cottages 3BR, Boat Parking, Walk to Marinas
A wooden picnic table with a pitcher, glasses, and a plate set on a grassy area by a body of water.

13. 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)
"We are a Family of 4 that stayed and absolutely loved Rosehill Cottage! Set back in a serene setting with the most beautiful view of the Rappahannock River! The Cottage was adorable with plenty of space to spread out, was clean, & had all of the cooking ware you need. The pool was a blast! We really enjoyed our time at the pool! I would definitely give Rosehill Cottage a consideration when you want to get away from the hustle & bustle of everyday life!"
United States
Melody F.
The price is €455
includes taxes & fees
25 Oct - 26 Oct
Waterfront Rappahannock River Cottage, Private Pool, Kayaks, Fire Pit & Garden
A dining area with a dark wooden table, white chairs, a modern chandelier, and framed artwork on the wall.

14. 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 €516
includes taxes & fees
4 Nov - 5 Nov
Waterfront Retreat with Office and Private Dock, Boats!
A house surrounded by dense greenery and a small dock extending into a body of water.

15. Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool
Exmore
10.0 out of 10, Exceptional, (77 reviews)
"It was a beautiful setting there. We loved the pool. Manager was very friendly n welcoming."
United States
Rita T.
The price is €424
includes taxes & fees
1 Nov - 2 Nov
Nassawadox Creek Waterfront Home with Private Pool
A room with a wooden floor, a sliding glass door leading to a deck with outdoor furniture, and a view of the ocean.

16. Waterfront Home with pool, dock, gameroom, and kayaks!

Waterfront Home with pool, dock, gameroom, and kayaks!
Topping
10.0 out of 10, Exceptional, (1 review)
"Beautiful property. Owner responded very quickly to questions and resolved problem quickly. Seems pricey. We enjoyed our time there. Very quiet."
United States
Patricia C.
The price is €950
includes taxes & fees
24 Oct - 25 Oct
Waterfront Home with pool, dock, gameroom, and kayaks!
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

Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

10/10 Excellent
"The cottage is truly a magical place, especially for those with a water-loving dog that also loves to roll or lay in the grass! We’ve been here multiple times, and as always, the cottage was in great shape and the host was so communicative and responsive—before, during, and after our stays. We always think about when we can return again after each of our stays. It’s truly a cozy and comfortable home away from home with magnificent views of the bay/river. Don’t miss the sunsets from the cottage!"
Ji B. 5-night trip
Posted 2 days ago
Waterfront Cottage w Private Beach on Chesapeake Bay!

Find out more about Gwynn

Gwynn Holiday Homes information

Number of reviews
415
Accommodation
173 Holiday Homes
Lowest Price
€186
Highest Price
€1,210