Wynne Holiday Rentals

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Holiday Rentals in Wynne

Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (54)
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Waterfront Reedville Home w/ Private Dock!
10.0 out of 10, Exceptional, (8)
"Very accommodating, comfy beds (a real +). Kitchen fully loaded with supplies (including spices and condiments). We spent so much time down on the dock crabbing and fishing. Our dogs loved the freedom and space. Made friends with others in the area and did dog walks with them."
Waterfront Reedville Home w/ Private Dock!
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, (75)
"This place is incredible!!!! What an amazing property and beautiful home."
Piney Point, private , Beach Front Cottage
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Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (46)
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
10.0 out of 10, Exceptional, (25)
"Beautiful! The home was very clean, and fully stocked with everything you'd need during your stay. Had a lot of fun visiting the nearby towns--definitely had the small-town atmosphere. The cell phone service presented a challenge though. The three of us whose carrier was Verizon had no problem at all, but the other party who had another carrier was unable to get a connection unless we went closer to town. Something to consider. Also, we were unable to get local channels/cable on the TV. Used...
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Virginia Retreat on Wicomico River w/ Dock!
10.0 out of 10, Exceptional, (7)
"Gorgeous location on the Great Wicomico!! Beautiful home with both a rustic feel and lovely modern additions. We brought our boat and the cove on Cole’s Creek was well protected with deep water. Property grounds were so nice, lots of space, and gorgeous view! The owner was super supportive and very helpful with recommendations in the area. Highly recommend!!"
Virginia Retreat on Wicomico River w/ Dock!
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is NZ$467
includes taxes & fees
10 Jun - 11 Jun
Soul Oasis - home on the Chesapeake Bay
Coan River Cottage w/ Fire Pit, Pool, Movie Room
10.0 out of 10, Exceptional, (2)
"Jen was helpful and accommodating to our last minute requests."
Coan River Cottage w/ Fire Pit, Pool, Movie Room
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
The Schultz Estate
9.6 out of 10, Exceptional, (5)
"This house is great for large groups with plenty of comfortable bedrooms, three bathrooms (note one is only a tub, no shower), and loads of outdoor seating and fire options. This is an old farmhouse, so quirks of an old wooden house on the Eastern shore come with that. Personal bug spray at this property is essential as the mosquitos are very intense. The owner did stop by to give us a lawn spray for them but we did not use it as I am a master naturalist and community garden manager who is...
The Schultz Estate
Cozy Virginia Potomac Riverfront Cottage
9.6 out of 10, Exceptional, (24)
"We had a wonderful stay. The house was just as described, a cozy cottage perfect for relaxing with beautiful riverfront views. The kitchen was stocked with everything we needed, the living room and main bedroom we used were comfortable, and the sun porch had great views where you could relax in the AC. The patio had a great dining table/umbrella, and the dock was perfect for fishing. Thank you for a lovely getaway cottage!"
Cozy Virginia Potomac Riverfront Cottage
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, (4)
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (171)
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
10.0 out of 10, Exceptional, (37)
"Great place to stay with a fantastic view. Kids loved all the activities to do at the home and property manager was wonderful to deal with and even went over the top with the welcome sign with our name on it. Highly recommend!"
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Rock Hall on the water
9.4 out of 10, Exceptional, (43)
"We had a great time in this home. It was extremely clean and perfect for our family. The huge yard was amazing. We had coffee on the porch as the sun came up. Very quiet and private. We definitely will go back!"
Rock Hall on the water
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, (9)
"The cabin itself was lovely with a southwestern feel. Very clean when we arrived and met our expectations. The outside space was the best! Even though it was a rainy weekend, we were able to take the kayaks out on the lake during a break in the rain. Unfortunately the weather prohibited us from visiting the beach but the property was close to Solomon's Island where there is plenty of shopping and dining. My only complaint was the mattress in the master bedroom. It felt wore out and we kind of...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
10.0 out of 10, Exceptional, (66)
"My family had a wonderful stay at Ivy Cove. We were in town for our niece’s wedding and it was close enough to participate in all family activities but far enough away to be a peaceful haven to relax. The house is beautiful. Beds were very comfortable. We really enjoyed the fire pit and game room. The owner was fantastic. We would absolutely stay again in this amazing home."
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"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!
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
10.0 out of 10, Exceptional, (26)
"Quick weekend getaway from Annapolis and wanted to bring the pups. Very dog friendly with great access to the water."
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
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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 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, (1005)
"great. convenient"
The price is NZ$168
includes taxes & fees
16 Jun - 17 Jun
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Hilton Garden Inn Solomons
3.0 star property
8.6 out of 10, Excellent, (529)
"Room temp was fine but temp in common spaces was very warm, no AC."
The price is NZ$200
includes taxes & fees
3 Jul - 4 Jul
Hilton Garden Inn Solomons
Country Inn & Suites by Radisson, Lexington Park (Patuxent River Naval Air Station), MD
2.5 star property
9.0 out of 10, Wonderful, (922)
"The carpet and furniture in the room could have been much cleaner. The couch and chair had dirt stains. "
The price is NZ$219
includes taxes & fees
14 Jun - 15 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wynne holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wynne. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wynne. Seeing all the best attractions is bound to make you fall in love with Wynne. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wynne short-term rentals, that won’t be hard to do.

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?

The Schultz Estate : This holiday home rental outside of Wynne offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Piney Point Beach.

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.

Recent reviews of Wynne properties
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