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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Gwynn cottages

A wooden dock leading to a house with a covered porch and outdoor seating.

1. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
9.8 out of 10, Exceptional, (51 reviews)
"Very peaceful. Loved the view. The house was set up nicely. Enjoyed our stay"
United States
Donna P.
$377 nightly
The price is $416
Oct 4 - Oct 5
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A wooden dock leading to a house with a covered porch and outdoor seating.

2. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
3.0 star property
Deltaville
$371 nightly
The price is $409
Oct 4 - Oct 5
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

3. 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, (95 reviews)
"Nice, relaxing stay! Just what we were looking for."
United States
Daniela R.
$327 nightly
The price is $364
Oct 8 - Oct 9
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

4. Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset
Cape Charles
9.4 out of 10, Exceptional, (24 reviews)
"Gorgeous property and excellent host!"
United States
Ryan M.
$381 nightly
The price is $444
Oct 6 - Oct 7
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.

5. 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.
$339 nightly
The price is $377
Oct 5 - Oct 6
Total with taxes and fees
The Waverly Tree House
A house with a large lawn, surrounded by tall trees.

6. Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Hayes
8.4 out of 10, Very good, (5 reviews)
"Great property. Waterfront with pier, huge yard, beautiful home with pool table, hot tub and projector set up. 100% would stay here again and recommend as would all of the family we had stay or visit us there. "
United States
Steve F.
$1,137 nightly
The price is $1,265
Oct 11 - Oct 12
Total with taxes and fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

7. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Oct 3 - Oct 4
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

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

Restored 1930s Cottage on 1 Acre w/ Fire Pit
3.0 star property
Hayes
$322 nightly
The price is $358
Oct 8 - Oct 9
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
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 house was perfect, to bad the weather wasn't the first three days we dealt with the nor'easter but it gave us time to rest. Monday night music at the Hole in the Wall was a nice surprise."
Sandi H. 4-night trip
Posted 3 days ago
Waterfront Cottage w Private Beach on Chesapeake Bay!

Find out more about Gwynn

Gwynn Cottages information

Number of reviews
173
Accommodation
79 Cottages
Lowest Price
$358
Highest Price
$1,265

Frequently asked questions

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If you want to fill up your itinerary in Gwynn, make tracks to Gwynn's Island Musuem. It's a winner with travelers and locals alike.

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