Holiday Homes in Gwynn

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Gwynn

"Bee Haven" Cottage Retreat Near Colonial Williamsburg
10.0 out of 10, Exceptional, (81)
"This adorably decorated home is situated in a quiet, tree-dense neighborhood with easy access to the highway if you’re spending the day outside of town. The town of Gloucester is quaint, filled with friendly people, and many dining options. The host made the stay easy, welcoming, and lovely. The home is absolutely sweet. Comfy decor, very clean, great kitchen, and comfy beds. Parking is ample and the views from every window are picturesque. The only “word of caution” is that the water does have...
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is NZ$1,291
includes taxes & fees
2 Dec - 3 Dec
Private 5-acre Waterfront Peninsula with Beach
Private Beach & Deck: Bayfront Home in Hayes!
10.0 out of 10, Exceptional, (12)
"If you’re looking for peace and quiet with your own small & private beach at the mouth of the York River, then this is the place for you! The house is new and beautifully appointed with every modern convenience you could want. TVs that operate off your own streaming accounts were in several rooms for you to use. Patrick, the host was so helpful with any questions we had. Although in a somewhat remote location, we were only 14 minutes from the Yorktown bridge and near all the historic sites as...
Private Beach & Deck: Bayfront Home in Hayes!
Waterfront Hartfield Vacation Rental w/ Dock!
9.8 out of 10, Exceptional, (15)
"We had a wonderful time staying here. This was more of a stay in and relax type vacation for us. House was very comfortable. I enjoyed fishing the pond "more like a small lake". Fishing from the dock was hit or miss but once we got in the supplied kayaks things, I started catching them left and right. Any questions we had were promptly answered by Kim the host. Don't hesitate to reach out to her, she's wonderful. We definitely plan on returning. Hopefully sooner rather than later. "
Waterfront Hartfield Vacation Rental w/ Dock!
Cozy Country setting with comforts of home
8.8 out of 10, Excellent, (15)
"Was very warm and inviting atmosphere. Easy to find and off the main traffic at the same time very convenient. "
Cozy Country setting with comforts of home
Cozy cottage on the Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"We so enjoyed our stay on the Piankatank. Sitting on pier morning, afternoon and evening was a delight. We’d definitely stay again. "
Cozy cottage on the Chesapeake Bay
Relaxing 1 bedroom 2019 Camper beside the Seven River
9.2 out of 10, Wonderful, (16)
"Camper was clean and cozy. A little hard to find and water on the road a little alarming. Property was not as clean as pictures presented. It was quite."
The price is NZ$250
includes taxes & fees
2 Dec - 3 Dec
Relaxing 1 bedroom 2019 Camper beside the Seven River
Enjoy family fun and Sunsets at Piankatank Point.
9.8 out of 10, Exceptional, (47)
"Quiet place, loved the water view"
Enjoy family fun and Sunsets at Piankatank Point.
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
9.6 out of 10, Exceptional, (18)
"The property is very secluded, You feel like the world is behind you. It is peaceful and quiet, The sound of nature will be the only symphony you’ll hear. I love the private beach area. We fished and caught some crab on the boat deck. The house is a bit old but that is where the charm is. There was some bug in the house but that was expected. Overall we had great time. "
The River House at Whitestone: Pet Friendly, Secluded Private Beach, w/ Kayaks!
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
9.8 out of 10, Exceptional, (156)
"Very nice house. I'd rent it again for a stay in the area. Not a place for families, but good for one or two couples. "
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Monthly discount- beautiful house, Gloucester VA
10.0 out of 10, Exceptional, (18)
"The house was great Very clean 2 friends shared King bed plenty of room Each bed was very comfortable and comfortable pillows "
Monthly discount- beautiful house, Gloucester VA
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
10.0 out of 10, Exceptional, (146)
"Stole away for a long weekend and this did not disappoint. Everything was perfectly cozy and relaxing - exactly what I was looking for. If I didn't live a 4 hour plane ride away, I think I'd be back more frequently; but I certainly will return!"
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Mid-century modern meets classic cape on the coast.
10.0 out of 10, Exceptional, (8)
"Clean comfy house in Mathews. Easy walk to restaurants, groceries and downtown shops. "
Mid-century modern meets classic cape on the coast.
Fantastic waterfront home on Jackson Creek
10.0 out of 10, Exceptional, (49)
"Nice place, interesting layout"
Fantastic waterfront home on Jackson Creek
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
9.8 out of 10, Exceptional, (121)
"I was in town for a couple nights as I was attending a meeting. I found the place to be cozy and convenient. It's just about a block away from a coffee house. I appreciated the character of the home and the design of the interior, which contributed to me feeling comfortable in the space. "
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly
10.0 out of 10, Exceptional, (92)
"Neat, clean, beautiful! Right on the water, blast crabbing, quiet… couldn’t have been better! Host is in touch and gracious. We’ll do it all again!"
Chesapeake Bay Waterfront: Kayaks, Fire Pit, Wifi, Bikes, Dog-friendly
Beach House on Chesapeake Bay!
10.0 out of 10, Exceptional, (121)
"Mathew’s is like home for me. I was not disappointed by this trip. We enjoyed Bay views, sitting on the deck and most importantly building community in the living room. What a great experience! I recommend this property for a couples getaway, families looking to getaway or a girls Trip. "
Beach House on Chesapeake Bay!
Huntington Farm - Great Family Retreat
9.6 out of 10, Exceptional, (54)
"Great place to stay and beautiful views. Was perfect for our group. Highly recommend!"
Huntington Farm - Great Family Retreat
Coco’s Cabana
9.6 out of 10, Exceptional, (26)
"The house had the perfect kitchen, great room, screen porch and terrace for me and my siblings to spend a weekend together during a larger family reunion. The owner provided clear and timely instructions for arrival and departure. There were plenty of supplies in the kitchen and bathrooms. The house and yard are well maintained and we loved having a dip in the pool! Plenty of off-street parking."
Coco’s Cabana
Spacious Mathews Retreat w/ Waterfront Views!
10.0 out of 10, Exceptional, (23)
"Extremely comfortable, well equipped home in a gorgeous location. Relaxing spot on the water with plenty of entertainment for all ages. Highly recommend. "
Spacious Mathews Retreat w/ Waterfront Views!
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.
Don't see what you're looking for?
See all available properties in Gwynn
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Gwynn

Waterfront Cottage with Private Beach, Sunsets over Water
10.0 out of 10, Exceptional, (193)
"It was a perfect spot for an intimate weekend getaway. The pups absolutely loved it, and Beaverdam park is close enough that we were able to get a nice long hoke in as well. "
Waterfront Cottage with Private Beach, Sunsets over Water
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
10.0 out of 10, Exceptional, (217)
"I’m not sure I can add anything more to the other reviews that are already out there. Clean and well kept, love the odds and ends that are stocked- so nice not to have buy a whole box of baggies to use one, or a set of salt and pepper for vacation use! Would be happy to stay again. "
Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free.
Private 5-acre Waterfront Peninsula with Beach
9.4 out of 10, Exceptional, (32)
"There were so many things to do at this beautiful location! We enjoyed boating, swimming, crabbing, disc golf, bonfires, games, and more! The house comfortably sleeps 21 people! It’s a lovely house that has an incredible view and it’s so quiet and relaxing. "
The price is NZ$1,291
includes taxes & fees
2 Dec - 3 Dec
Private 5-acre Waterfront Peninsula with Beach
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.