Book Holiday Homes in Gwynn

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Featured Holiday Homes in Gwynn

Private Beach & Deck: Bayfront Home in Hayes!

Private Beach & Deck: Bayfront Home in Hayes!

Hayes
Located in Hayes, this vacation home is on the waterfront, within a 15-minute drive of Crown Pointe Marina and Gloucester County Public Library.
Private Beach & Deck: Bayfront Home in Hayes!
Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Weems
Located in Weems, this vacation home is within a 10-minute drive of Historic Christ Church and Compass Entertainment Complex.
Riverfront Virginia Home - Dock, Fire Pit & Kayaks
Small Town Getaway - close to in-town Mathews with a casual rural life

Small Town Getaway - close to in-town Mathews with a casual rural life

Mathews
A stay at this vacation home places you in the heart of Mathews, and within a 10-minute drive of Gwynn's Island Musuem.
Small Town Getaway - close to in-town Mathews with a casual rural life
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Waterfront Hartfield Vacation Rental w/ Dock!

Waterfront Hartfield Vacation Rental w/ Dock!

Hartfield
Located in Pine Top, this vacation home is on the waterfront, within a 15-minute drive of Piankatank River Golf Club and Middlesex County Museum.
Waterfront Hartfield Vacation Rental w/ Dock!
Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool

Exmore
With a stay at this vacation home in Exmore, you'll be on the waterfront, and 30 mi (48.4 km) from Cape Charles Beach and 10.3 mi (16.6 km) from Exmore Town ...
Nassawadox Creek Waterfront Home with Private Pool
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Gloucester
Located in Gloucester, this vacation home is in a rural location, within a 15-minute drive of Fairfield Foundation and Gloucester Public Library.
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Chesapeake Bay Beachfront Retreat

Chesapeake Bay Beachfront Retreat

White Stone
With a stay at this vacation home in White Stone, you'll be on the beach, and 8.5 mi (13.7 km) from White Stone Beach and 8.9 mi (14.2 km) from Steamboat Era ...
Chesapeake Bay Beachfront Retreat
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

Hayes
Located in Hayes, this vacation home is on the waterfront, within a 10-minute drive of Cuba Island and Gloucester County Public Library.
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Cozy cottage on the Chesapeake Bay

Cozy cottage on the Chesapeake Bay

Hallieford
When you stay at this vacation home in Piankatank, you'll be on the waterfront and 14 minutes by car from Gwynn's Island Musuem.
Cozy cottage on the Chesapeake Bay
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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
162 Holiday Homes
Lowest Price
AU$176
Highest Price
AU$201
Popular accommodation
Private Beach & Deck: Bayfront Home in Hayes!, Riverfront Virginia Home - Dock, Fire Pit & Kayaks, Small Town Getaway - close to in-town Mathews with a casual rural life, Waterfront Hartfield Vacation Rental w/ Dock!, Nassawadox Creek Waterfront Home with Private Pool, "Bee Haven" Cottage Retreat Near Colonial Williamsburg, Chesapeake Bay Beachfront Retreat, Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg., Cozy cottage on the Chesapeake Bay

Top trending hotels in Gwynn

Waterfront Cottage with Private Beach, Sunsets over Water

Waterfront Cottage with Private Beach, Sunsets over Water

Grimstead
You'll be centrally located in Gwynn with a stay at this cottage, and 15 minutes by foot from Gwynn's Island Musuem.
Waterfront Cottage with Private Beach, Sunsets over Water
Gwynn's Island Renovated 1910 Farm House & Sand Beach

Gwynn's Island Renovated 1910 Farm House & Sand Beach

Gwynn
When you stay at this vacation home in Gwynn, you'll be near the beach and within a 5-minute drive of Gwynn's Island Musuem.
Gwynn's Island Renovated 1910 Farm House & Sand Beach
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 AU$201 per night from 4 May to 5 May
AU$201
includes taxes & fees
4 May - 5 May
A stay at Holiday Inn Express Gloucester by IHG places you in the heart of Gloucester, a 4-minute drive from Gloucester Museum of History and 11 minutes from ...
Holiday Inn Express Gloucester by IHG
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Camp Cardinal Gloucester Point

Camp Cardinal Gloucester Point

2.5 out of 5
3149 Campground Rd, Hayes, VA
The price is AU$176 per night from 15 Apr to 16 Apr
AU$176
includes taxes & fees
15 Apr - 16 Apr
Located in Hayes, Camp Cardinal Gloucester Point is within a 10-minute drive of Woodville Park and Gloucester County Public Library.
Camp Cardinal Gloucester Point
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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.