Wynne Holiday Rentals

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Holiday Rentals in Wynne

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

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

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

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10.0 out of 10, Exceptional, (50)
"We had a chance to spend the weekend with our kids (age 18 and 20), and we couldn't have asked for a better location. The view was spectacular and the home was perfect. It was so peaceful and relaxing, yet there was so much to do—fishing, kayaking, paddleboarding, ping-pong, darts, board games, the list goes on. Everyone had a fantastic time. The only problem is that were only there for three nights!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (18)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is NZ$511
includes taxes & fees
29 Dec - 30 Dec
Soul Oasis - home on the Chesapeake Bay

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"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

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

10.0 out of 10, Exceptional, (15)
"House is perfect for families to get together for a holiday. Has pretty much everything you need."
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Waterfront Reedville Home w/ Private Dock!

10.0 out of 10, Exceptional, (14)
"Lovely home on large property. Easy walk to the dock. River area was beautiful. Large screened in porch was very nice. Sunrise on the river was amazing. Highly recommend!"
Waterfront Reedville Home w/ Private Dock!

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, (16)
"My mom didn’t want to leave. Beautiful family retreat. Quiet and restful. "
Virginia Retreat on Wicomico River w/ Dock!

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

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.

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"The home and property are exactly as advertised. I loved being five minutes away from Point Lookout, the sunset views, and the waterfront. "
Secluded River Front Cottage

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

10.0 out of 10, Exceptional, (40)
"The house was amazing clean and functional. "
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

10.0 out of 10, Exceptional, (183)
"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**

Historic Hoopersville Getaway on Chesapeake Bay!

9.6 out of 10, Exceptional, (10)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (57)
"My friend and I stayed for the weekend and had a lovely time. The property is quiet and secluded, and the beach area is very cute. Dog friendly is also a plus."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Rock Hall on the water

9.4 out of 10, Exceptional, (47)
"Rock Hall is a beautiful property that is nicely situated between several quaint towns. We loved the space and the large yard for the kids and dog to run. I do feel that it was a bit overpriced for what the house offers. In contrast to other rentals I found this to be quite stark and lacking in the comforts that I look for during a stay. The house is very minimally furnished and there were no comfort items to be found. It would have been nice to have a flashlight for walking through the...
Rock Hall on the water
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, (1002)
"the hotel staff was kind and attentive"
The price is NZ$179
includes taxes & fees
26 Dec - 27 Dec
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, (525)
"It was a nice experience everyone was nice, Ari at the front desk was Avery inviting and welcomed my family and baby. It was an 6.5 drive so we were exhausted. All the guest were very friendly as well. Super clean, good breakfast. Restaurants easy 2 min way. Great experience overall "
The price is NZ$202
includes taxes & fees
5 Jan - 6 Jan 2025
Holiday Inn Express & Suites Lexington Park-California, an IHG Hotel

Hilton Garden Inn Solomons

3.0 star property
8.6 out of 10, Excellent, (568)
"Pool is closed "
The price is NZ$220
includes taxes & fees
1 Jan - 2 Jan 2025
Hilton Garden Inn Solomons
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.

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 Historic St. Mary's City and St. Mary's College of Maryland.

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.