Book Holiday Homes in Gwynn

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Featured Holiday Homes in Gwynn

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Bohannon VA
Stay at this beach holiday home in Westville. Enjoy free Wi-Fi, a beach locale and 2 outdoor pickleball courts. Popular attractions Bethel Beach Natural Area ...
Opens in a new windowExperience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Cobbs Creek VA
Stay at this holiday home in Piankatank. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Gwynn's Island Musuem and Deltaville Marina are ...
Opens in a new windowKimary Cove - Waterfront Relaxation and NO CLEANING FEE
Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay

Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay

FOSTER VA
Stay at this family-friendly holiday home in Westville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bethel Beach Natural Area Preserve ...
Opens in a new windowVictorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay
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Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Gwynn's Island VA
Stay at this beach holiday home in Gwynn. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Gwynn's Island Musuem and Deltaville Marina are ...
Opens in a new windowPeaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

North VA
Stay at this holiday home in Westville. Enjoy a water park, laundry facilities and patios. Popular attraction Brown Park is located nearby.
Opens in a new windowCharming 2-bedroom house with AC, WiFi in Mathews County Virginia
Spacious waterfront home with dock and sunset view

Spacious waterfront home with dock and sunset view

Kilmarnock VA
Stay at this holiday home in Kilmarnock. Enjoy a garden, laundry facilities and patios. Popular attractions Golden Eagle Golf Club and Hughlett Point Natural ...
Opens in a new windowSpacious waterfront home with dock and sunset view
Mid-century modern meets classic cape on the coast.

Mid-century modern meets classic cape on the coast.

Moon VA
Stay at this holiday home in Westville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bethel Beach Natural Area Preserve and Gwynn's ...
Opens in a new windowMid-century modern meets classic cape on the coast.
Enjoy family fun and Sunsets at Piankatank Point.

Enjoy family fun and Sunsets at Piankatank Point.

Saluda VA
Stay at this holiday home in Saluda. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Thousand Trails Beach Park and Piankatank River Golf ...
Opens in a new windowEnjoy family fun and Sunsets at Piankatank Point.
Little Bay Waterfront Retreat

Little Bay Waterfront Retreat

White Stone VA
Stay at this beach holiday home in White Stone. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions White Stone Beach and Golden Eagle Golf Club ...
Opens in a new windowLittle Bay Waterfront Retreat
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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.

Gwynn Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gwynn vacation homes are the perfect way for you to wing it.

Holiday houses in Gwynn let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gwynn in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gwynn adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gwynn with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gwynn vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gwynn Holiday Homes essential information

Accommodation
153 Holiday Homes
Lowest Price
NZ$183
Highest Price
NZ$188
Popular accommodation
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!, Kimary Cove - Waterfront Relaxation and NO CLEANING FEE, Victorian Farmhouse w/ private waterfront & pier at the mouth of Mobjack Bay, Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!, Charming 2-bedroom house with AC, WiFi in Mathews County Virginia, Spacious waterfront home with dock and sunset view, Mid-century modern meets classic cape on the coast. , Enjoy family fun and Sunsets at Piankatank Point., Little Bay Waterfront Retreat

Top trending hotels in Gwynn

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Grimstead VA
Stay at this beach cottage in Gwynn. Enjoy free Wi-Fi, a beach locale and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowGwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Gwynn's Island VA
Stay at this beach holiday home in Gwynn. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Gwynn's Island Musuem and Deltaville Marina are ...
Opens in a new windowPeaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is NZ$183 per night from 26 Dec to 27 Dec
NZ$183
26 Dec - 27 Dec
includes taxes & fees
Stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowHoliday Inn Express Gloucester by IHG
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Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 11 Jan to 12 Jan
NZ$188
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowHampton Inn Gloucester
Don't see what you're looking for?
See all available properties in Gwynn
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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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^Subject to availability and chosen travel dates.