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
Book a stay at this beach vacation home in Hayes. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Hog Island and Big Island are ...
Private Beach & Deck: Bayfront Home in Hayes!
Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Weems
Book a stay at this family-friendly vacation home in Weems. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Steamboat Era ...
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
Stay at this vacation home in Mathews. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Bethel Beach and Bethel Beach Natural ...
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
Book a stay at this family-friendly vacation home in Pine Top. Enjoy a pool table, patios, and cable/satellite TV service. Popular attractions Piankatank River ...
Waterfront Hartfield Vacation Rental w/ Dock!
Nassawadox Creek Waterfront Home with Private Pool

Nassawadox Creek Waterfront Home with Private Pool

Exmore
Stay at this vacation home in Exmore. Enjoy free WiFi, private pools, and a garden. Popular attractions Horse Island and South Island are located nearby.
Nassawadox Creek Waterfront Home with Private Pool
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Gloucester
Stay at this vacation home in Gloucester. Enjoy a water park, a garden, and patios. Popular attractions Brown Park and Gloucester Public Library are located ...
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Chesapeake Bay Beachfront Retreat

Chesapeake Bay Beachfront Retreat

White Stone
Book a stay at this beach vacation home in White Stone. Enjoy a beach locale, patios, and cable/satellite TV service. Popular attractions Deltaville Maritime ...
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
Book a stay at this beach vacation home in Hayes. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Allens Island and Cuba Island are located ...
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Cozy cottage on the Chesapeake Bay

Cozy cottage on the Chesapeake Bay

Hallieford
Stay at this vacation home in Piankatank. Enjoy free WiFi, a garden, and patios. Popular attractions Gwynn's Island Musuem and Deltaville Marina are located ...
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
160 Holiday Homes
Lowest Price
NZ$197
Highest Price
NZ$222
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
Book a stay at this beach cottage in Gwynn. Enjoy free WiFi, a beach locale, and a water park. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Stay at this vacation home in Gwynn. Enjoy free WiFi, a garden, and patios. Popular attractions Gwynn's Island Musuem and Holly Point Nature Park are located ...
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 NZ$222 per night from 4 May to 5 May
NZ$222
includes taxes & fees
4 May - 5 May
Stay at this 3.5-star business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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 NZ$197 per night from 16 Apr to 17 Apr
NZ$197
includes taxes & fees
16 Apr - 17 Apr
Book a stay at this family-friendly cabin in Hayes. Enjoy free parking, an outdoor pool, and cable TV channels. Popular attractions Severn Yachting Center and ...
Camp Cardinal Gloucester Point
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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.