Gwynn, VA Cottage Rentals from $351

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

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Our top choices for Gwynn cottages

A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

1. Radiant Gloucester House w/ Private Porch!

Gloucester

$322 nightly

Oct 7 - Oct 8

Total with taxes and fees

A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

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

Hayes

Susan C.

$315 nightly

Oct 8 - Oct 9

Total with taxes and fees

A wooden deck with a white fence and a lounge chair, overlooking a calm body of water during sunset.

3. Smith Beach cottage w/ private sunset

Cape Charles

Ryan M.

$381 nightly

Oct 12 - Oct 13

Total with taxes and fees

A wooden deck with a chair, a welcome mat, and a view of a forest.

4. The Waverly Tree House

Machipongo

Jeanna C.

$324 nightly

Oct 7 - Oct 8

Total with taxes and fees

A house with a large lawn, surrounded by tall trees.

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

Hayes

Steve F.

$1,137 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

Hayes

$322 nightly

Oct 8 - Oct 9

Total with taxes and fees

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Top Gwynn Hotel Reviews

Warner Hall

10/10 Excellent

"Quite possibly the best impromptu stop my husband and I have ever made! Everything was incredibly clean, comfortable, and thoughtfully equipped with everything we needed. Breakfast was even more enjoyable with the beautiful view.We loved taking in the beautifully decorated rooms and especially enjoyed cozying up by all the fireplaces. The entire stay was so peaceful and relaxing—it was the perfect place to get away and unwind. We’re already planning our return!"

Hampton Inn Gloucester

8/10 Good

"Overall this was a great choice. I was visiting family nearby and didn't spend a lot of time in the hotel, so I gave a good rating for some of the categories as I didn't get to try them. The hotel was easy to find and located very near an outdoor shopping mall with good chain restaurant choices, a Walmart, TJ Maxx and other stores. Within walking distance of the hotel are a Wendy's and Chipotle. The area felt very safe. Check-in was great, the lobby is very clean. The hotel staff were friendly. When we got to our room, there was a slight bleach smell and I would rather that than a moldy smell. The bathroom and room were clean and lots of towels. Beds were very comfortable. I didn't eat the breakfast, my son did and said it was great. I would definitely stay here again."

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

10/10 Excellent

"Here’s a warm, natural version:We had such a wonderful stay at Kim’s VRBO! The place was absolutely adorable, extremely clean, and even nicer than we expected. Everything felt well cared for, comfortable, and welcoming. We really enjoyed our stay and would absolutely recommend Kim’s place to anyone looking for a clean, cozy, and beautiful place to stay. We would definitely stay again!"

Gwynn's Island Gem | Private Beach & Bay Views

10/10 Excellent

"We ABSOLUTELY loved our stay here. Beautiful views, peaceful, accommodating...it was all of the things. The rooms were spacious, the master bed was nothing short of amazing! So comfortable!The deck needs a little attention, but it certainly served it's purpose, and we enjoyed sitting out at night with family talking and enjoying the solitude. Being on the island is like taking a step back in time, and it truly embodies a traditional coastal community. We loved every minute of our stay and will be back!"

Find out more about Gwynn

Gwynn Cottages information

Number of reviews	122
Accommodation	80 Cottages
Lowest Price	$351
Highest Price	$1,265

Frequently asked questions

Why book your cottage in Gwynn with Expedia?

Expedia has some great cottages in Gwynn, so get ready for a memorable vacay 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 travelers and locals alike.

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Things to do in Coastal Virginia

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Our top choices for Gwynn cottages

1. Radiant Gloucester House w/ Private Porch!