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

Search Gwynn Cottages

Check prices for these dates

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

Our top choices for Gwynn cottages

A white house with a black front door, a small porch, and a gravel driveway.

1. 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.
$431 nightly
The price is $475
Oct 21 - Oct 22
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

2. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Oct 25 - Oct 26
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.

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)
"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.
$331 nightly
The price is $368
Oct 21 - Oct 22
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)
"Peaceful and quiet with amazing views!"
United States
Eileen D.
$381 nightly
The price is $444
Oct 21 - Oct 22
Total with taxes and fees
Smith Beach cottage w/ private sunset
A house with a large lawn, surrounded by tall trees.

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.
$1,102 nightly
The price is $1,227
Oct 21 - Oct 22
Total with taxes and fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
A wooden deck with a chair, a welcome mat, and a view of a forest.

6. 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.
$300 nightly
The price is $334
Oct 21 - Oct 22
Total with taxes and fees
The Waverly Tree House
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

7. 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 21 - Oct 22
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

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

8/10 Good
"The staff was very nice"
Jackie 3-night trip
Posted 4 days ago
Holiday Inn Express Gloucester by IHG

Find out more about Gwynn

Gwynn Cottages information

Number of reviews
122
Accommodation
80 Cottages
Lowest Price
$334
Highest Price
$1,227

Frequently asked questions

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What is there to do in Gwynn near my cottage?
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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