Gwynn Holiday Rentals

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Holiday Rentals in Gwynn

Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
Property grounds
Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
10.0 out of 10, Exceptional, (180)
"Location is perfect for families with small children — beach access is a few feet away and the bay water is shallow/calm. Property is well-kept and has everything you could need. Loved our stay and will definitely be back."
Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (212)
"This is our second stay at this home. The home provided enough room for our family of 5. Three young adults stayed in the second BR. And, we managed fine with the 1 Bath. The home is comfortable and provided a wonderful getaway. The home was stocked with all the things that we needed to enjoy our week on the island."
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
Fridge, microwave, oven, stovetop
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
8.0 out of 10, Very good, (2)
"The location on Gwynn’s Island was beautiful. The spacious cottage was lovely, well furnished, and with every amenity. The fenced in yard was beautifully landscaped and plenty of room for the children to run around and explore. With use of the golf cart the beach was a few minutes away. Location was very quiet and very relaxing. Having 2 full bathrooms was a plus with 2 kids. Everything was perfect and owners were most accommodating. Thank you."
The price is HK$2,732
per night
29 Jun - 30 Jun
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
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Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
Aerial view
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
9.6 out of 10, Exceptional, (38)
"Great location. Private beach. Nice quiet neighborhood."
Private Beach - Spacious Dog & Family Friendly Beachfront 4 Bedroom River House
Cottage on a Private Island in the York River
Exterior
Cottage on a Private Island in the York River
10.0 out of 10, Exceptional, (304)
"My husband, chihuahua and I stayed at the cottage for 4 days while in Virginia. We loved the view of the water from all the windows that allowed natural light in. We watched all the birds and crabs while sitting on the back porch. The location is great for visiting all the Historic areas. We took a segway tour and Ghost tour in Yorktown. We spent a whole day walking around in Williamsburg. Being a history buff my husband really enjoyed it. I even learned a few things. LOL I would recommend...
Cottage on a Private Island in the York River
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Exterior
Restored 1920's Cottage on 1 Acre w/ Fire Pit
9.4 out of 10, Exceptional, (45)
"My daughter, granddaughter and I stayed for 3 nights. It was wonderful. I wish we could have stayed longer."
Restored 1920's Cottage on 1 Acre w/ Fire Pit
Mobjack Bay Rental on Private Cove!
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!
Waterfront Topping Vacation Home w/ Boat Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Topping Vacation Home w/ Boat Dock!
10.0 out of 10, Exceptional, (6)
"Great place to unwind, relax, spend quality with the family. Bill’s “Rivah house” was clean and has all the essentials we needed for a great weekend. Enjoyed hanging out on the deck, fishing and crabbing on the dock, and kayaking! Bill is great host and communicated with us early, Hope to come back soon!"
Waterfront Topping Vacation Home w/ Boat Dock!
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Fridge, microwave, oven, stovetop
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
9.4 out of 10, Exceptional, (107)
"The house is very big and accommodating. The yard and beach access was a major plus. There was a cockroach inside which was slightly off putting but not a huge deal. We requested sheets which they kindly provided. Communication was great and check in/out was seamless."
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Oceanfront White Stone Cottage w/ Private Beach!
Property grounds
Oceanfront White Stone Cottage w/ Private Beach!
7.4 out of 10, Good, (63)
"Nice"
Oceanfront White Stone Cottage w/ Private Beach!
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Fridge, microwave, oven, stovetop
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (66)
"Perfect neighborhood - quiet and secluded yet close to town. The home has everything you need and is super cute - we loved the bee decorations. We’ve never stayed in a rental that was as clean as Bee Haven - super impressed by my neat freak self! We were also able to enjoy evening walks with our dog on Ware Neck Road. Thank you for the hospitality!"
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Private 5-acre Waterfront Peninsula with Beach
Property grounds
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (28)
"I held my daughters 18th birthday party here, and it was incredible! Plenty of room for hanging out and great for overnight guests (lots of rooms and places to sleep). Beautiful house, inside and out! Lots of things to keep people busy and entertained, but just as many for relaxing. Fantastic stay overall with a wonderful host!!! Would absolutely recommend."
The price is HK$4,628
per night
10 Jul - 11 Jul
Private 5-acre Waterfront Peninsula with Beach
Radiant Gloucester House w/ Private Porch!
Interior
Radiant Gloucester House w/ Private Porch!
9.8 out of 10, Exceptional, (12)
"Beautifully restored interior. Air conditioning worked great. Quiet street but only steps to Main Street. Especially good for visiting residents at Riverside Sanders which is just a block away."
Radiant Gloucester House w/ Private Porch!
Walk to Town Restaurants. 1st floor King Bed & Walk in Shower! Fire Pit🔥!
Sun-loungers, beach towels
Walk to Town Restaurants. 1st floor King Bed & Walk in Shower! Fire Pit🔥!
10.0 out of 10, Exceptional, (22)
"We came to the area for our granddaughter’s graduation and it was only minutes from the high school. It was in close proximity to quite a few good restaurants and downtown Mathews! The host was quick to reply to any questions or comments that we had. If the opportunity presented itself, we would definitely stay here again!"
The price is HK$1,319
per night
14 Jul - 15 Jul
Walk to Town Restaurants. 1st floor King Bed & Walk in Shower! Fire Pit🔥!
Room on river with sunset views and private beach!
Sun-loungers
Room on river with sunset views and private beach!
10.0 out of 10, Exceptional, (19)
"Our rental was amazing. We had everything we needed. The view, comfort, cleanliness, weather and terrific Hosts."
Room on river with sunset views and private beach!
Monthly discount- beautiful house, Gloucester VA
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
Mid-century modern meets classic cape on the coast.
Exterior
Mid-century modern meets classic cape on the coast.
10.0 out of 10, Exceptional, (4)
"Very comfortable setting. Good location for nearby venues. Enjoyed our stay."
Mid-century modern meets classic cape on the coast.
Private, 7-acre waterfront retreat on Winter Harbor Haven
Property grounds
Private, 7-acre waterfront retreat on Winter Harbor Haven
10.0 out of 10, Exceptional, (115)
"It was fantastic!! Beautiful property, clean well cared for home rental very well equipped. Felt like home ❤️hosts were also very nice and welcoming, responding to my inquiries very fast. We will definitely come back!"
Private, 7-acre waterfront retreat on Winter Harbor Haven
Relaxing 1 bedroom 2019 Camper beside the Seven River
Interior
Relaxing 1 bedroom 2019 Camper beside the Seven River
9.8 out of 10, Exceptional, (10)
"Although the actual camper was not the one advertised, our stay was filled with all the expected amenities Kimberly described. In a previous review someone mentions the rooster, he was quite pleasant, not at all like described in their review. The camper behind ours was closer than I would expect and not in the description, but it was not a total bother, I just adjusted the shades appropriately for privacy. Kimberly & her family were AMAZINGLY FRIENDLY! My 4yo was invited to meet the children,...
The price is HK$656
per night
10 Jul - 11 Jul
Relaxing 1 bedroom 2019 Camper beside the Seven River
Water front Oasis with pickle-ball court and hot tub
Property grounds
Water front Oasis with pickle-ball court and hot tub
10.0 out of 10, Exceptional, (1)
"Had a great experience staying at the property. It was as clean and well maintained. The host Jessica was a delight to work with."
The price is HK$11,383
per night
13 Jul - 14 Jul
Water front Oasis with pickle-ball court and hot tub
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

Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
Property grounds
Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
10.0 out of 10, Exceptional, (180)
"Location is perfect for families with small children — beach access is a few feet away and the bay water is shallow/calm. Property is well-kept and has everything you could need. Loved our stay and will definitely be back."
Waterfront Cottage with Private Beach, Pet Friendly - 1 Week Left this August!
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Property grounds
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (212)
"This is our second stay at this home. The home provided enough room for our family of 5. Three young adults stayed in the second BR. And, we managed fine with the 1 Bath. The home is comfortable and provided a wonderful getaway. The home was stocked with all the things that we needed to enjoy our week on the island."
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
Fridge, microwave, oven, stovetop
Cozy little home on Gwynn's Island with Chesapeake Bay semi-private beach access
8.0 out of 10, Very good, (2)
"The location on Gwynn’s Island was beautiful. The spacious cottage was lovely, well furnished, and with every amenity. The fenced in yard was beautifully landscaped and plenty of room for the children to run around and explore. With use of the golf cart the beach was a few minutes away. Location was very quiet and very relaxing. Having 2 full bathrooms was a plus with 2 kids. Everything was perfect and owners were most accommodating. Thank you."
The price is HK$2,732
per night
29 Jun - 30 Jun
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.

Search for holiday rentals in Gwynn on Expedia! You can easily find your home rentals, villas, holiday apartments in Gwynn using one of the methods below:

  • View our selection of featured holiday rentals in Gwynn
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Look no further and take a look at our great range of rental properties in Gwynn!

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

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

5/5 Excellent
‘Bee’utiful Cottage
"Perfect neighborhood - quiet and secluded yet close to town. The home has everything you need and is super cute - we loved the bee decorations. We’ve never stayed in a rental that was as clean as Bee Haven - super impressed by my neat freak self! We were also able to enjoy evening walks with our dog on Ware Neck Road. Thank you for the hospitality!"
A verified traveller stayed at "Bee Haven" Cottage Retreat Near Colonial Williamsburg
Posted 4 days ago
"Bee Haven" Cottage Retreat Near Colonial Williamsburg