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Our top choices for Gwynn cottages

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 AU$568
includes taxes & fees
10 Nov - 11 Nov
Riverfront Cottage: Fire Pit & Kayaks

2. 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 AU$652
includes taxes & fees
10 Nov - 11 Nov
Bay Dream Believer Cottage on Beautiful East River Waterfront

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, (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 AU$502
includes taxes & fees
10 Nov - 11 Nov
Restored 1930s Cottage on 1 Acre w/ Fire Pit

4. 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 Waverly Tree House

5. 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.
The price is AU$1,731
includes taxes & fees
10 Nov - 11 Nov
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

6. 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 AU$603
includes taxes & fees
10 Nov - 11 Nov
Smith Beach cottage w/ private sunset

7. Located in the Heart of Gloucester Courthouse!

Located in the Heart of Gloucester Courthouse!
3.0 star property
Gloucester
The price is AU$532
includes taxes & fees
12 Nov - 13 Nov
Located in the Heart of Gloucester Courthouse!

8. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
The price is AU$522
includes taxes & fees
10 Nov - 11 Nov
Radiant Gloucester House w/ Private Porch!

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

Restored 1930s Cottage on 1 Acre w/ Fire Pit
3.0 star property
Hayes
The price is AU$522
includes taxes & fees
10 Nov - 11 Nov
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.

Learn more about Gwynn

This historic Chesapeake Bay village invites you to explore its waterfront charm and maritime heritage at the Gwynn's Island Museum. Rent kayaks to paddle the calm waters, then ask locals about their favourite seafood spots serving fresh-caught blue crabs.

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

Frequently Asked Questions

What is there to do in Gwynn near my cottage?

You'll find loads of awesome things to fill your days in Gwynn. Explore popular attractions like Bethel Beach, Deltaville Marina and Gwynns Island Musuem. Deltaville Maritime Museum, Bethel Beach Natural Area Preserve and Holly Point Nature Park are also on many to-do lists.