Holiday houses in Mechanicsville

5 out of 5 average rating, 75 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

4.93 out of 5 average rating, 203 reviews

Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

4.93 out of 5 average rating, 15 reviews

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

4.95 out of 5 average rating, 19 reviews

Home in Coltons Point

The Eventide at Serenity Lane

Kick back and relax in this charming, stylish and fully renovated ‘55 bungalow. Situated in view of beautiful and tranquil Potomac River in historic St Mary’s County Maryland. Enjoy stunning water views in a professionally designed luxury home with gourmet kitchen. Coltons Point is a quiet village-like community with nearby marinas and creeks perfect for boating, fishing, crabbing and a birder’s paradise. Site of the first landing of English Colonials in 1633 and a quaint local history museum

4.88 out of 5 average rating, 273 reviews

Guest suite in La Plata

Beautiful Rural Suite near Washington, D.C.

Enjoy a rural environment only 50 minutes outside of Washington, D.C., and 45 minutes away from Andrew's Air Force Base. Located in a quiet wooded neighborhood with horses, goats, ducks, and more this property allows children space to run and play. Stores are less than 10 minutes down the road. This is a perfect little haven, fully equipped with a kitchen and laundry facilities. Parking is available for boats and trailers. Please Note: Sunday check-in is at 4pm, unless requested otherwise.

Guest suite in Mechanicsville

5 out of 5 average rating, 16 reviews

Private Walkout In-Law Suite

Enjoy completely private walkout basement suite in home at end of country road. Has 1 bedroom, kitchen and bath. Enjoy views of local farms and horses. Home owners live on main floor and are available if needed. NO smoke/vape. Must be able to use stairs. Great location for contractors, travelers and interns working at PAX, Calvert Cliffs or St. Marys Hospital. Relax on back patio surrounded by tall trees. Easy access to all of Southern Marylands charms or drive into DC/VA for sightseeing.

5 out of 5 average rating, 33 reviews

Private, Lakefront Oasis- Lavinia by the Lake

This home is the embodiment of true Southern Maryland waterfront living. It is the best location for Rockfish, crabbing and oystering!The house is fully gated so you will always have peace of mind while your kids and pets wander around. This 5 bedroom, 3 bathroom stunner with a full walk out basement is perfect for the larger water loving family who loves to entertain. The outdoor living space hits all the marks: upper and lower deck, umbrellas throughout, a Gazebo bar, Hot Tub and more.

5 out of 5 average rating, 117 reviews

Home in Leonardtown

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

4.98 out of 5 average rating, 135 reviews

Apartment in Leonardtown

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

4.93 out of 5 average rating, 159 reviews

Guesthouse in Bushwood

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

5 out of 5 average rating, 44 reviews

Guesthouse in Brandywine

Quiet cottage in the woods. King-bed suite.

Take it easy at this unique and tranquil getaway. Open floor plan with all the modern conveniences. King size bed, with space for an additional queen size air mattress. Washer, dryer, shower/bathtub. Note, there is no smoking or vaping allowed inside the Cottage, and absolutely no "4/20" products allowed on the property. Two night minimum for all reservations, and due to documented medical allergy concerns we are unable to host pets/animals of any kind.

4.89 out of 5 average rating, 130 reviews

Home in Waldorf

*Brand New | Modern | Lux 4 BR | Huge | 24 m to DC

Dee's Lounge will offer you the ULTIMATE perfect stay! Indulge in a luxurious and refined experience that is sure to leave you feeling refreshed, relaxed, and rejuvenated! This space is designed to make you feel like you've escaped your everyday life. Whether it's a girl trip, family time or hanging with your friends, you are sure to have an amazing time! We are readily available to accommodate your needs and make sure that you enjoy your time here!

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Other great holiday rentals in Mechanicsville

4.96 out of 5 average rating, 70 reviews

Home in Newburg

Beautiful, serene waterfront property

JonathanRating, 5 stars1 month ago

An incredible peace of property! This house has been beautifully renovated and exceeded every expectation. Unbelievable waterfront views from nearly every room in the house, back porch and fire pit. Also a very nice surprise of having a little play area stocked with toys for the little ones! This is a must stay if we’re ever back in the area!

Apartment in White Plains

5 out of 5 average rating, 10 reviews

Spacious Next Gen Suite.

DanielaRating, 5 stars3 days ago

We had an amazing stay at Theo’s place! Everything was perfect clean, comfortable, and exactly as described. The thoughtful touches and great communication made our trip so enjoyable. We’d absolutely love to return! Highly recommend!

4.86 out of 5 average rating, 7 reviews

Home in Prince Frederick

Chesapeake Escape

MicheleRating, 5 stars1 week ago

Diana’s place was perfect for our family. The house had many of the items we would have had to bring from home. You can tell she wanted people to feel at home and be comfortable. My grandbabies loved the books. The neighbors were friendly. The neighborhood was nice to get a quick walk in before the day started.

5 out of 5 average rating, 6 reviews

Home in Charlotte Hall

Cozy Retreat w/ Pool: MIR & DC

NicoleRating, 5 stars1 month ago

This place was great! Justin was a GREAT host and the home was exactly what we needed while we were in town. The printed instructions on the fridge greatly helped us with the checkout procedures. The house was peaceful and cozy!

4.59 out of 5 average rating, 190 reviews

St. Mary's County Home with a View

TereRating, 5 stars3 weeks ago

This place was an amazing home. Just like the pictures. Bed's were comfy, there was a lot of room and enough bathrooms. The view of the river was nice. The home was clean and cool when we walked in. We enjoyed the Jenga blocks. And not having TVs in the rooms was a good idea. lol.. just to fall asleep after being out and about. We had a great time, thank you for letting us experience at great vacation in your home. Just wish it was so overcast, would have been nice to see all the stars.

Guest suite in Mechanicsville

5 out of 5 average rating, 9 reviews

Suite Magnolia - Private Country Setting -

JoanRating, 5 stars13 months ago

Cheryl and Don are wonderful hosts. She was very good at communication and checked in a few times. The home is in a quiet and safe area. The airbnb was very nice. It was nicely done, pretty and very comfortable. There is everything you need to cook meals. It was located well for getting to different parts of the area. I stayed for a little over a week. I would definitely recommend this lovely airbnb.

Guesthouse in Mechanicsville

4.99 out of 5 average rating, 88 reviews

Barnyard Retreat

AutumnRating, 5 stars1 month ago

I can’t say enough about the owners! Extremely helpful and nice. The pictures don’t do it justice. Very cozy and comfortable and it felt just like home! Will definitely be back soon!