Holiday Rentals in Wynne

  • 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

Check prices for these dates

Holiday Rentals in Wynne

The Schultz Estate

8.4 out of 10, Very good, (15)
"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

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

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is €574
includes taxes & fees
18 Feb - 19 Feb
4-BR Waterfront Turret Home

2 Bedroom Cozy Beach Cottage with Beach Access

10.0 out of 10, Exceptional, (12)
"This was a great little cottage and was perfect for our stay. We wanted to be close to Valey Lee and the location was great. We will definitely consider staying again."
2 Bedroom Cozy Beach Cottage with Beach Access

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

'river's Edge Retreat With Kayaks & River Access!

3.0 star property
'river's Edge Retreat With Kayaks & River Access!

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

10.0 out of 10, Exceptional, (211)
"We loved UpYonda! Erin and Mark are so nice and easy to communicate with. The home is beautiful and there really is everything you need there. The suite upstairs is beautiful and huge!! The view of the water is amazing and the wildlife was stunning. We saw a fox, Blue Heron and got video of an Otter rolling around in the snow on the dock! The stargazing is fantastic and we made a snowman. We loved it. "
Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

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

10.0 out of 10, Exceptional, (17)
"Great stay, easy check-in/check-out, highly recommend"
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

El Camino

10.0 out of 10, Exceptional, (33)
"Very cute cabin. We enjoyed the peace and quiet. Ver close to our destin.ation, Point lookout."
El Camino

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

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.

Hays Beach House - Hot Tub - Private Beach

10.0 out of 10, Exceptional, (4)
"We booked this bayside property for a short family vacation and the house and amenities were exactly what we needed during our time at Hays Beach. There were ample bedrooms and spaces for all of us to relax, the kitchen was well appointed. The beach in front of the house was perfect for our grandson to play in a small pool while the others lounged in chairs or were in the water directly in front of the house. The public beach was a short walk away and we enjoyed seeing all the wildlife on the...
Hays Beach House - Hot Tub - Private Beach

Bay Estate by AvantStay | Waterfront, Private Pond

10.0 out of 10, Exceptional, (1)
"Such a beautiful house, very nice for family or friends get together."
Bay Estate by AvantStay | Waterfront, Private Pond

Waterfront Solomons Apartment

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. liked the view. We had a problem with the door lock Anthony was quick to get it resolved!"
The price is €242
includes taxes & fees
18 Feb - 19 Feb
Waterfront Solomons Apartment

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

9.8 out of 10, Exceptional, (32)
"Very nice and quiet. We were there end of December. "
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

When you want to get away from everything Magnolia shores 2 acres of tranquility

10.0 out of 10, Exceptional, (65)
"Great time with great hosts! "
When you want to get away from everything Magnolia shores 2 acres of tranquility

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (9)
"I loved this sweet A frame home! Celebrated my 48th birthday with a girls' trip and we all loved it. Enjoyed fires and Christmas movies each night. House has a lot of space and is so comfortable. Loved the views of the Bay, particularly from the sunroom and porch. Found quite a bit of sea glass on the neighborhood beach, as well as at the house beach during low tide. Owner was incredibly responsive and went above and beyond. Great place. Would highly recommend. "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"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 €277
includes taxes & fees
18 Feb - 19 Feb
Soul Oasis - home on the Chesapeake Bay
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 Wynne
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Wynne you may be interested in

Solomons Inn Resort & Marina

2.5 star property
8.0 out of 10, Very good, (751)
"Only stayed one night to attend a private cooking class at No Thyme to Cook. The Inn was Super cozy and clean. They even had non dairy milk. The front desk staff were friendly and very helpful. We had a great stay. "
The price is €138
includes taxes & fees
16 Mar - 17 Mar
Solomons Inn Resort & Marina

Quality Inn Solomons - Beacon Marina

2.5 star property
7.6 out of 10, Good, (735)
"It was quiet "
The price is €98
includes taxes & fees
25 Feb - 26 Feb
Quality Inn Solomons - Beacon Marina

Holiday Inn Express & Suites Lexington Park-California by IHG

2.5 star property
9.2 out of 10, Wonderful, (535)
"Clean. Pleasant people "
The price is €122
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Express & Suites Lexington Park-California by IHG
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 Dennis Point Marina and Historic St. Mary's City.

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.