Best Cottages in Gwynn in 2026

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

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Our top choices for Gwynn cottages

The Waverly Tree House

Machipongo

Jeanna C.

includes taxes & fees

7 Jul - 8 Jul

Smith Beach cottage w/ private sunset

Cape Charles

includes taxes & fees

3 Aug - 4 Aug

Riverfront Cottage: Fire Pit & Kayaks

Deltaville

Donna P.

includes taxes & fees

6 Jul - 7 Jul

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

Hayes

Steve F.

includes taxes & fees

11 Jul - 12 Jul

Cottage (2 Bedrooms) | Front of property

Riverfront Cottage: Fire Pit & Kayaks

Deltaville

includes taxes & fees

6 Jul - 7 Jul

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Top Gwynn Hotel Reviews

Hampton Inn Gloucester

10/10 Excellent

"I enjoyed my stay as always..No complaints..!!"

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

10/10 Excellent

"My mother and I so enjoyed our stay at Kim's in Cobbs Creek. This was my mother's first Airbnb experience. Because of Kim's attention to detail, my mother will no longer stay in a hotel ever again. Kim goes above and beyond and thinks of absolutely everything you possibly may need or forgotten. It defiantly was home away from home. The next time we come to visit the area we most certainly plan on staying agin."

The Little Blue Cottage - Topping : Waterfront!

8/10 Good

"The floors were dirty in the way that you couldn’t see dirt, but if you walked barefoot you could feel it was gritty and it made our feet dirty. One evening we looked out the window and a man was just outside changing the filter on the water filtration system. It was getting dark and it was alarming to see a strange man in the yard. There were cameras in the carport and on the back of the house that could presumably see through the windows of the house. This felt like a major lack of privacy. The beach down the road had signs that said ‘locals only’ which felt hostile. We were strictly instructed not to step to the right of the driveway which is the exact property line because the neighbors would be upset. This felt uncomfortable. We had a nice time on our trip and made use of the kayaks but the rack holding the kayaks was unstable and fell over when my husband took the kayaks down to use."

Charming 2-bedroom house on the Chesapeake Bay

8/10 Good

"The house is so charming and is in a very peaceful area. The house itself could use some care for paint and outside power wash. Opening the blinds lots of cobwebs outside in the windows. Kitchen is very well stocked with everything you need to cook and eat with. The house inside was decently clean, however we found several cobwebs hanging from lights and in corners. We love that the house was pet friendly and lots of room for our lab to run around outside. Also would have liked some citronella candles so we could have sat outside in the evening."

Find out more about Gwynn

Gwynn Cottages information

Number of reviews	55
Accommodation	80 Cottages
Lowest Price	£306
Highest Price	£961

Frequently asked questions

Why book your cottage in Gwynn with Expedia?

Expedia has some great cottages in Gwynn, so get ready for a memorable holiday close to nature. If you need to stick to a budget, select how much you're willing to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with a pool or a kitchen. We'll help you find the right digs whatever your trip looks like.

How can I find cheap cottages in Gwynn?

The simplest way to uncover cheap cottages in Gwynn is with Expedia's user-friendly filter tool. Narrow down your search results by star rating, amenities and budget to nab awesome bargains in just a few clicks.

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 travellers and locals alike.

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Room 1

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Check prices for these dates

Our top choices for Gwynn cottages

The Waverly Tree House

Smith Beach cottage w/ private sunset

Riverfront Cottage: Fire Pit & Kayaks

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

Riverfront Cottage: Fire Pit & Kayaks

Find holiday rentals that suit your style

Top Gwynn Hotel Reviews

Hampton Inn Gloucester

Quality Inn Kilmarnock

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Bubba Butler's Cottage

The Little Blue Cottage - Topping : Waterfront!

Perfect for long-term workers & short stays—comfort, style & convenience await!

Charming 2-bedroom house on the Chesapeake Bay

Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail w 1/2 Labor Day weekend!

Smith Beach cottage w/ private sunset

Find out more about Gwynn

Gwynn Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Gwynn Cottages

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gwynn cottages

The Waverly Tree House

Smith Beach cottage w/ private sunset

Riverfront Cottage: Fire Pit & Kayaks

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

Riverfront Cottage: Fire Pit & Kayaks

Find holiday rentals that suit your style

Top Gwynn Hotel Reviews

Hampton Inn Gloucester

Find out more about Gwynn

Gwynn Cottages information

Frequently asked questions

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