Holiday Rentals in Gwynn

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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, (178)
"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 €386
per night
29 May - 30 May
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
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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
9.4 out of 10, Exceptional, (27)
"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.
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
Sun-loungers
Room on river with sunset views and private beach!
10.0 out of 10, Exceptional, (17)
"Lovely"
Room on river with sunset views and private beach!
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, (62)
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (113)
"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
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!
Aerial view
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
9.6 out of 10, Exceptional, (37)
"Had a great stay, with little to no complaints!"
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
Property grounds
Monthly discount- beautiful house, Gloucester VA
10.0 out of 10, Exceptional, (13)
"We visit the area a lot to see family so I've stayed in quite a few rentals here. This is my first time at this property and I would stay again. Looks just like the listing. I appreciate the simple layout for our needs. 3 bedrooms meant we were comfortable at night. I thought the one king bed was pretty soft and the other firm; both comfy just think that's helpful to some to know. The living area and kitchen/dining space aren't huge but again you should know that from the pictures and it worked...
Monthly discount- beautiful house, Gloucester VA
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!
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 €295
per night
3 Jun - 4 Jun
Welcome to this Waterfront Home with Amazing Views
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
Exterior
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
9.8 out of 10, Exceptional, (61)
"I met up with a good friend for a long weekend that immediately felt too short. The house is absolutely wonderful! Views galore. Total peace and tranquility. Very private. We just wanted to enjoy the cove, drink coffee by the water and enjoy excursions to Gloucester, Gwynn Island, and Mathews. The house was perfectly located but was wonderful just one its own. We hope to come back soon and take out the kayaks in the warmer weather."
Tranquility on the Water! Renovated Modern Farmhouse on Private Cove on N. River
Exterior
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (44)
"Our grandchildren came for several visits and overnights. It was great. The cottage is very user friendly and was quiet. The surrounding areas uncluding paddock was a bonus for our Shetland sheepdogs. The walking trails were fine. We had a fantastic stay."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Don't see what you're looking for?
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, (178)
"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 €386
per night
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.

Everything you need to know about Gwynn holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gwynn holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gwynn holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gwynn holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gwynn. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gwynn holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gwynn holiday rentals we have selected for you start as low as €295 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gwynn rentals

At Expedia, we put the best Gwynn holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gwynn rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gwynn holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gwynn. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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