Gwynn Holiday Rentals

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Holiday Rentals in Gwynn

Property grounds
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (210)
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Fridge, microwave, oven, stovetop
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
6.0 out of 10, (1)
"The property was nice but i would call it pet tolerant, not friendly. I booked this for my children and there two dogs instead of hotel. If i had known all the rules before i booked i wouldn't have. Out of two nights, they only stayed one because they couldn't relax with their animals."
The price is NZ$669
includes taxes & fees
29 May - 30 May
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
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Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (303)
"Spectacular location. Unbelievable views. Extremely well appointed house."
Cottage on a Private Island in the York River
Fridge, microwave, oven, stovetop
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, (106)
"We all - seniors to toddlers - enjoyed our stay here! Wonderful to be on the river, and also convenient to Williamsburg!"
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Property grounds
Private 5-acre Waterfront Peninsula with Beach
9.6 out of 10, Exceptional, (25)
"We had a great time staying here and will certainly look to stay again in the future! 5 stars!"
Private 5-acre Waterfront Peninsula with Beach
Outdoor spa tub
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (38)
"Everything you want to do is right there at the house..Fishing, crabbing. Canoeing, kayaking and so much more. Already planning a trip back this summer."
Enjoy family fun and Sunsets at Piankatank Point.
Property grounds
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
9.6 out of 10, Exceptional, (14)
"Cannot beat this location. The private beach was just incredible. We came with two dogs who enjoyed going for a swim each morning. The kids loved hanging out on the beach all day. The hosts were responsive and thoughtful. When we arrived the first night the lights were on and music was gently playing. Thoughtful touches that were very much appreciated. We could not have hoped for a better experience."
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
Property grounds
Historic Cottage on Ware River Estate
10.0 out of 10, Exceptional, (242)
"Cute cabin. Porch was perfect in the morning. Listening to the birds while drinking coffee was relaxing. Location was perfect as we have family in Onemo. It was a relaxing & perfect."
Historic Cottage on Ware River Estate
Fridge, microwave, stovetop, dishwasher
Waterfront Topping Vacation Home w/ Boat Dock!
10.0 out of 10, Exceptional, (5)
"Very much enjoyed our stay!! Great views and great location. Don’t forget to play ping pong in the garage!"
Waterfront Topping Vacation Home w/ Boat Dock!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (112)
"Pet friendly well kept property with more amenities than others we’ve stayed in when it comes to outdoor activities, kitchen supplies/gadgets to the outdoor dog bowl. Quiet and private location with nice views from porches and even inside. We enjoyed our stay and so did our pups. 1 day with bad weather and it didn’t matter we had movie marathon and a great view. Some hunting dogs would come visit and make our girls wonder further than normal but zero complaints otherwise. Premium beds and...
Private, 7-acre waterfront retreat on Winter Harbor Haven
Fridge, microwave, oven, stovetop
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (62)
"Seriously, don't think twice about booking this property! It's in a beautiful, quiet setting and about an hour drive from countless attractions. We went to Williamsburg, short 45 minute drive through beautiful country. The property is exceptional! The host has thought of literally everything and well appointed. Looking forward to returning soon!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Fridge, microwave, oven, stovetop
Welcome to this Waterfront Home with Amazing Views
10.0 out of 10, Exceptional, (13)
"Our stay was great! The host gave us all the information we needed, and the property was amazing. We spent plenty of time talking and reading out on the water while enjoying the view. This property is quiet and fairly secluded but also doesn't feel far from food and entertainment. We loved our stay and would recommend this location to anyone!"
The price is NZ$520
includes taxes & fees
4 Jun - 5 Jun
Welcome to this Waterfront Home with Amazing Views
Property grounds
Waterfront Hartfield Vacation Rental w/ Dock!
9.8 out of 10, Exceptional, (9)
"Absolutely loved this place. Quiet, secluded and so relaxing. We enjoyed the view and listening to nature. Owner was wonderful. I highly recommend staying here."
Waterfront Hartfield Vacation Rental w/ Dock!
Property grounds
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (61)
"The property is older but cute definitely waterfront with an amazing view."
Oceanfront White Stone Cottage w/ Private Beach!
Interior
Amazing views of the Chesapeake Bay.
10.0 out of 10, Exceptional, (10)
"We were in town for a reunion with good friends and former neighbors. This cottage was perfect for our needs! Spacious and comfortable. Kitchen stocked with everything you might need. Great view of the river and a covered front porch to sit and enjoy it! Lovely area to walk around as well. Host very responsive! I would definitely stay here again. Highly recommend!"
Amazing views of the Chesapeake Bay.
Outdoor pool
Nassawadox Creek Waterfront Home with Private Pool
10.0 out of 10, Exceptional, (31)
"All girls weekend was a great success. The house was clean and comfortable. Very vintage style. The view was great."
Nassawadox Creek Waterfront Home with Private Pool
Property grounds
The Little Blue Cottage - Topping : Waterfront!
9.8 out of 10, Exceptional, (29)
"Little blue cottage was perfect. We wouldn’t change a thing. So nicely appointed and such a beautiful location."
The Little Blue Cottage - Topping : Waterfront!
Property grounds
Mobjack Bay Rental on Private Cove!
10.0 out of 10, Exceptional, (2)
"The home was very comfortable and very peaceful. The amenities were wonderful! Very clean. The owner was responsive and kind. We would come back every time!"
Mobjack Bay Rental on Private Cove!
Beach
Sunflower Cottage - Waterfront; Outdoor shower!
10.0 out of 10, Exceptional, (2)
"The dock and view were spectacular!! The bathroom shower was tiny. We aren’t big, but a full size man would have had issues."
Sunflower Cottage - Waterfront; Outdoor shower!
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See all available properties in Gwynn
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.

Other types of properties in Gwynn you may be interested in

Property grounds
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
10.0 out of 10, Exceptional, (177)
"Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back."
Gwynn's Island Cottage: Waterfront w Private Beach, Pets Ok-2 Weeks in Aug Open!
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (210)
"We love this place... it's our third time there and it's always clean and feels like home. Big plus.... we get to take our dog. ❤️"
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Fridge, microwave, oven, stovetop
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
6.0 out of 10, (1)
"The property was nice but i would call it pet tolerant, not friendly. I booked this for my children and there two dogs instead of hotel. If i had known all the rules before i booked i wouldn't have. Out of two nights, they only stayed one because they couldn't relax with their animals."
The price is NZ$669
includes taxes & fees
29 May - 30 May
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gwynn holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gwynn. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gwynn. Seeing all the best attractions is bound to make you fall in love with Gwynn. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gwynn short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Gwynn?

Yes, there are holiday rentals close to the most popular sights in Gwynn, or you can select a more secluded option if you're looking for a relaxing stay. Gwynn is known for its museums.

What are some of the best holiday rentals that Gwynn has to offer?

Private 5-acre Waterfront Peninsula with Beach: This holiday home rental outside of Gwynn is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Gwynn?

Choose from 13 Expedia holiday rentals in Gwynn for a memorable holiday.

What can I see and do in Gwynn?

Explore the area and family-friendly sights such as Deltaville Maritime Museum, or get out into nature at a spot like White Stone Beach. In the wider area, you’ll find Gwynn's Island Musuem and Deltaville Marina.

What are holiday rentals like in Gwynn?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gwynn. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.

Recent reviews of Gwynn properties
Expedia verified reviews