Book Holiday Homes in Gwynn

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Featured Holiday Homes in Gwynn

Heart of Irvington w/Fireplace Walk to Tides Inn &  restaurants - Dog friendly!

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Irvington
Stay at this vacation home in Irvington. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowHeart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Irvington's BEST WATERFRONT EXPERIENCE!.  Walk to Tides Inn & Irvington shops.

Irvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops.

Irvington
Stay at this vacation home in Irvington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Steamboat Era Museum and Historic Christ Church ...
Opens in a new windowIrvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops.
Spacious waterfront home with dock and sunset view

Spacious waterfront home with dock and sunset view

Kilmarnock
Stay at this vacation 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
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Serenity on the Rappahannock

Serenity on the Rappahannock

White Stone
Stay at this vacation home in White Stone. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Deltaville Maritime Museum and Holly Point ...
Opens in a new windowSerenity on the Rappahannock
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
Book a stay at this beach vacation home in Westville. Enjoy free WiFi, a beach locale, and 2 outdoor pickleball courts. Popular attractions Bethel Beach Natural ...
Opens in a new windowExperience the Best of Mathews Riverfront Living here at Mariner's Legacy!
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.
Opens in a new windowNassawadox Creek Waterfront Home with Private Pool
Enjoy family fun and Sunsets at Piankatank Point.

Enjoy family fun and Sunsets at Piankatank Point.

Saluda
Stay at this vacation home in Saluda. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thousand Trails Beach Park and Piankatank River ...
Opens in a new windowEnjoy family fun and Sunsets at Piankatank Point.
MILLION $ VIEWS NO EXTRA CHARGE!  HOT TUB! POOL! BEACH!  RESORT-LIKE AMENITIES!

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Hallieford
Book a stay at this beach vacation home in Piankatank. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the property condition in our reviews. ...
Opens in a new windowMILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
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 laundry facilities. Popular attractions Gwynn's Island Musuem and Deltaville Marina ...
Opens in a new windowCozy 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
156 Holiday Homes
Lowest Price
NZ$202
Highest Price
NZ$204
Popular accommodation
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!, Irvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops., Spacious waterfront home with dock and sunset view, Serenity on the Rappahannock, Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!, Nassawadox Creek Waterfront Home with Private Pool, Enjoy family fun and Sunsets at Piankatank Point., MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES! , Cozy cottage on the Chesapeake Bay

Top trending hotels in Gwynn

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

Gwynn's Island Cottage-Waterfront w Your Own 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 ...
Opens in a new windowGwynn's Island Cottage-Waterfront w Your Own 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
Book a stay at this beach vacation home in Gwynn. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Gwynn's Island Musuem and Holly Point Nature ...
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$204 per night from 3 Dec to 4 Dec
NZ$204
3 Dec - 4 Dec
includes taxes & fees
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. ...
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$202 per night from 30 Nov to 1 Dec
NZ$202
30 Nov - 1 Dec
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.