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
A stay at this vacation home places you in the heart of Irvington, just a 3-minute walk from Steamboat Era Museum and within a 5-minute drive of Historic Christ ...
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
A stay at this vacation home places you in the heart of Irvington, a 2-minute drive from Steamboat Era Museum and 5 minutes from 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
Located in Kilmarnock, this vacation home is on the waterfront, within a 15-minute drive of Chesapeake Bay and Good Luck Cellars.
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
When you stay at this vacation home in White Stone, you'll be on the waterfront and within a 5-minute drive of Chesapeake Bay.
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
With a stay at this vacation home in Westville, you'll be on the beach, and 12.9 mi (20.7 km) from Gwynn's Island Musuem and 13.5 mi (21.7 km) from Ware Parish ...
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
When you stay at this vacation home in Exmore, you'll be on the waterfront and 5 minutes by car from Chesapeake Bay.
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
When you stay at this vacation home in Saluda, you'll be on the waterfront and 13 minutes by car from Middlesex County Museum.
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
When you stay at this vacation home in Piankatank, you'll be on the beach and 12 minutes by car from Gwynn's Island Musuem.
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
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.
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
AU$177
Highest Price
AU$179
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
Located in Gwynn, this cottage is on the waterfront, within a 5-minute drive of Gwynn's Island Musuem and Chesapeake Bay.
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
With a stay at this vacation home in Gwynn, you'll be on the beach, a 1-minute walk from Chesapeake Bay and a 2-minute drive from Gwynn's Island Musuem.
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 AU$179 per night from 3 Dec to 4 Dec
AU$179
3 Dec - 4 Dec
includes taxes & fees
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 ...
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 AU$177 per night from 30 Nov to 1 Dec
AU$177
30 Nov - 1 Dec
includes taxes & fees
With a stay at Hampton Inn Gloucester in Gloucester, you'll be a 5-minute walk from Shoppes at Gloucester and 9 minutes by foot from Gloucester Youth ...
Opens in a new windowHampton Inn Gloucester
Don't see what you're looking for?
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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.