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House holiday rentals in Southern Maryland

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Top-rated house rentals in Southern Maryland

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Home

4.89 out of 5 average rating, 224 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million old+ shark teeth, and a fossil cliff beach. Fishing! Seasonal hot tub on patio! Bald eagle sightings! Theater Room!

Home

4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

"Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take a kayak out after breakfast to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acre in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home (w. 1GB hi-speed internet).

Guest favourite

Home

4.92 out of 5 average rating, 12 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.

Guest favourite

Home

4.96 out of 5 average rating, 26 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Home

4.85 out of 5 average rating, 119 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Guest favourite

Home

4.9 out of 5 average rating, 112 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

Guest favourite

Home

4.94 out of 5 average rating, 119 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Guest favourite

Home

5 out of 5 average rating, 119 reviews

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

Guest favourite

Home

4.94 out of 5 average rating, 191 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Guest favourite

Home

4.95 out of 5 average rating, 149 reviews

Water ft Chesapeake Bay DREaM Vacation Dock Kayaks

PLEASE READ ENTIRE LISTING You’ll have the option of booking: The main house ONLY with 2 bedrooms & 2 baths &/OR add the guest house providing an additional bedroom and one and 1/2 full bath. THE PRICE QUOTED IS FOR THE MAIN HOUSE ONLY. The guest house is $120 a night or $700 per week. Please scroll down to "message host" before requesting to book a reservation if you want to reserve both houses, if not, the guest house will need to be paid separately.

Guest favourite

Home

4.98 out of 5 average rating, 121 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Guest favourite

Home

5 out of 5 average rating, 28 reviews

Greystone Manor-Magnificently restored! Sleeps 10

Enjoy this magnificently renovated home in the center of town in Colonial Beach. Every inch of this house has been renovated and re-styled with a mix of the past and present. This home boasts 3 large bedrooms (1 King bed with ensuite, 2 Queen beds) and a large loft with 4 twin beds that would make every tweenager delighted! Each bedroom and living space has smart-TV's, and there is plenty of room to entertain and enjoy the outdoor spaces.

Holiday rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Hotels

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Popular amenities for house rentals in Southern Maryland

Free parking on premises

Air conditioning

House rentals with a pool

Home

4.91 out of 5 average rating, 139 reviews

House in Edgewater Maryland

Home

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Guest favourite

Home

4.96 out of 5 average rating, 112 reviews

Spend Christmas at Gorgeous, Waterfront Home!

Guest favourite

Home

4.99 out of 5 average rating, 144 reviews

Beach Please! River cottage w/private beach & dock

Guest favourite

Home

4.96 out of 5 average rating, 163 reviews

6BR Modern Home w/HEATED Pool & Screened in Porch

Guest favourite

Home

4.92 out of 5 average rating, 131 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

Guest favourite

Home

4.99 out of 5 average rating, 197 reviews

The Little Gypsy BoHome

Guest favourite

Home

5 out of 5 average rating, 125 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Weekly house rentals

Home

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

Guest favourite

Home

4.95 out of 5 average rating, 175 reviews

Beautiful Capitol Hill Row House

Guest favourite

Home

4.92 out of 5 average rating, 52 reviews

Light-Filled Victorian Town-Home

Guest favourite

Home

4.9 out of 5 average rating, 113 reviews

Gift House: Quiet, self check in & free Parking

Home

5 out of 5 average rating, 34 reviews

Dameron Farm on the Water - Private Pool

Home

4.7 out of 5 average rating, 115 reviews

Private Basement/Apartment with Separate Entry

Home

4.89 out of 5 average rating, 150 reviews

Kent Island Beautiful 4 BR home, central location!

Guest favourite

Home

4.98 out of 5 average rating, 103 reviews

140ft Dock, Pet-Friendly 8 Acre Waterfront Oasis !

Private house rentals

Home

4.93 out of 5 average rating, 40 reviews

Private Peninsula, Slice of Heaven! Kayak, Fishin

Guest favourite

Home

5 out of 5 average rating, 8 reviews

New Cozy Home In NW DC Sleeps 12

Guest favourite

Home

5 out of 5 average rating, 7 reviews

Rappahannock Cottage at MS

Guest favourite

Home

4.98 out of 5 average rating, 51 reviews

Cozy 2-level home with 2 bedrooms and an office.

Guest favourite

Home

4.98 out of 5 average rating, 53 reviews

Entire Beach House with Pool and Hot Tub

Guest favourite

Home

4.95 out of 5 average rating, 223 reviews

Great Historic Cambridge Home With Parking!

Guest favourite

Home

4.8 out of 5 average rating, 127 reviews

Gorgeous Chateau Style Home/Mansion

Guest favourite

Home

4.97 out of 5 average rating, 29 reviews

7BD Amazonia Duplex

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