Wynne Holiday Rentals

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Holiday Rentals in Wynne

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is NZ$536
includes taxes & fees
24 Nov - 25 Nov
Soul Oasis - home on the Chesapeake Bay

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

9.8 out of 10, Exceptional, (31)
"very quiet, peaceful, relaxing location. The house had everything we needed. We would definitely stay there again."
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Belle of the Chesapeake Bay

9.6 out of 10, Exceptional, (9)
"We initially booked due to location (we have family in the neighborhood). We are so glad we did! The property had plenty of space for 6 and offered rest and relaxation after a busy wedding weekend. The only con I can think of with the property is that all bathrooms are on the smaller side. The comfort, convenience, and amenities offered far outweighs this. This property is sure to become our go to when visiting the area. "
Belle of the Chesapeake Bay

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

El Camino

10.0 out of 10, Exceptional, (31)
"The place was phenomenal. Very clean. Very awesome to stay there. If you ever want to see the most beautiful sunset you have to go there. Plus the fishing was a lot of fun. Me and my husband really enjoyed the few days that we were there. Communication very good people. Very nice! That stayed next to us. I would definitely go back"
El Camino

Cozy Virginia Potomac Riverfront Cottage

9.8 out of 10, Exceptional, (34)
"This is a nice little cottage, tucked away from everything right on the river. I was looking for some peace and quiet, and that’s exactly what I got. Even though the weather wasn’t great, the sunroom still let me enjoy the views. "
Cozy Virginia Potomac Riverfront Cottage

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island

The Schultz Estate

8.8 out of 10, Excellent, (14)
"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"
The Schultz Estate

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!

Waterfront Reedville Home w/ Private Dock!

10.0 out of 10, Exceptional, (13)
"beautiful location. outside porch was great"
Waterfront Reedville Home w/ Private Dock!

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (63)
"Beautifully appointed cottage. Literally right on the water. Quiet, serene and relaxing. Loved it and will be back!"
Private Beach Front Getaway at The Sunshine Beach Cottage.

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (72)
"Great location. Spacious and clean. Easy checking in and communicate with owner."
Stunning secluded Luxury waterfront cottage with private deep water pier!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

10.0 out of 10, Exceptional, (14)
"I was in charge of booking my very first family vacation and I really wanted to be near water and trees. This location was perfect as the kids loved being on the beach (and utilizing the Kayaks, Life Jackets, and Floaties provided by the host) and the adults loved the serenity of the area. The host was very quick to respond to any questions I had which definitely set the tone for me before even arriving! "
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8 near Smith Point Marina

10.0 out of 10, Exceptional, (21)
"We loved this cute house. It was modernly decorated, had everything we needed and then some. We loved the quite of the country, but not really in country! and close to the marina we were heading for the next day. Reelin' and Relaxin' is very fitting name for the house and the area. Our only concern was house is not on a heavy traffic road, but cars zipped by quite fast for a dead end road."
The price is NZ$679
includes taxes & fees
10 Dec - 11 Dec
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8 near Smith Point Marina

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

10.0 out of 10, Exceptional, (36)
"We wanted a family vacation and looked for a place on Chesapeake Bay. My son and daughter found this place and we reserved it. The house is beautiful. Has everything one would want. The location is great although it’s a bit of a drive to anywhere. Our plan was to spend most of the time at the house and in the bay. However that didn’t happen. First the weather didn’t cooperate as it rained most of the week. In addition there was an invasion of jellyfish. They were terrible! My grandchildren were...
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier

Virginia Retreat on Wicomico River w/ Dock!

10.0 out of 10, Exceptional, (15)
"Beautiful home with a great blend of modern and rustic! Amazing spot to see sunrises and sunsets too. We enjoyed the porch, fully stocked kitchen and comfortable family room. "
Virginia Retreat on Wicomico River w/ Dock!

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (182)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (10)
"This was the perfect cottage for our family's fall getaway to St. Mary's! The host was wonderfully communicative and the cottage was perfectly appointed for our little get away. We will definitely be back!"
2 Bedroom Cozy Beach Cottage with 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.
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Other types of properties in Wynne you may be interested in

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1056)
"Great place and good breakfast for $85/night!"
The price is NZ$176
includes taxes & fees
27 Nov - 28 Nov
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

2.5 star property
9.2 out of 10, Wonderful, (519)
"Great service "
The price is NZ$204
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD

2.5 star property
9.0 out of 10, Wonderful, (971)
"Loved the room, it was clean and spacious !"
The price is NZ$192
includes taxes & fees
6 Dec - 7 Dec
Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Wynne?

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

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

Large waterfront cabin, kayaks & paddle boards, fire pit. Crabbing and fishing!: This holiday home rental outside of Wynne is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Wynne?

While exploring the area, visit family-friendly sights like Kinsale Museum, or get outside and enjoy nature at Point Lookout State Park. In the wider area, you’ll find St. Mary's College of Maryland and Elms Beach Park.

What are holiday rentals like in Wynne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Wynne. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.