Holiday rentals in Lake Shore

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Top-rated holiday rentals in Lake Shore

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.

Home in Arnold

Rachel's BnB

A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

ValueFamilyCheck-in

4.89 out of 5 average rating, 159 reviews

Top guest favourite

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

FamilyLocationOutdoor spaces

4.97 out of 5 average rating, 477 reviews

Top guest favourite

A well-lit living area features a black piano along one wall, with a wooden cabinet displaying books and decorations nearby. A fireplace is set within a white brick surround, and a flat-screen TV is mounted above. Comfortable seating is arranged for relaxation.

Guest suite in Arnold

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

FamilyLocationSleep quality

4.96 out of 5 average rating, 767 reviews

Top guest favourite

Home in Pasadena

Waterfront, FirePit, HotTub, GameRoom, PetFriendly

Picture yourself waking up to stunning views of the waterfront and spacious yard, while sipping a fresh warm coffee! Or enjoy a soak in the private hot tub while watching the sunset. For those sports fans we offer a 75" TV and pool table in the well-equipped game room. The outdoor area features a spacious dining setup, perfect for al fresco meals, and a fire pit for evenings of warmth and conversation. Whether you’re lounging by the water or entertaining, this property is the ultimate retreat!

LocationFamilyLaundry

4.97 out of 5 average rating, 79 reviews

Top guest favourite

Home in Pasadena

Waterfront Retreat | Pool, Hot Tub & Creek Views

Escape to the perfect waterfront retreat where boating, golf, and unforgettable sunsets come together. Nestled on a protected deep-water shoreline, this beautifully appointed home features a private deep-water pier with ample space for your boat, making it the ideal destination for anglers, cruisers, and anyone who loves life on the water. Less than 3 miles from premier 36-hole public golf course, return to relax in the sauna or by the pool then stroll to a waterfront restaurant for seafood!

LocationFamilyKitchen

5.0 out of 5 average rating, 11 reviews

Guest favourite

A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.

Flat in Pasadena

Relaxing Waterfront Apartment!

Welcome to our Bayhouse StayApartment! Our waterfront getaway features a large dock where you can relax on Adirondack chairs and soak in the beautiful water views! Enjoy kayaking (we have 2 for your use) and feel free to bring your own non motor watercrafts. Roast marshmallows in the our Gazebo's fireplace Inside the apartment you will find a beautiful updated kitchen, comfortable living room, 2 bedrooms and a bonus loft area Full bathroom is upstairs, and downstairs has a half bath.

LocationFamilyGrill

4.98 out of 5 average rating, 56 reviews

Guest favourite

An aerial view reveals a round above-ground pool surrounded by a spacious wooden deck. Loungers and an umbrella are positioned for relaxation. The lush yard features greenery, with a two-story house in the background, partially shaded by trees. A kayak rests nearby, suggesting potential water activities.

Home in Pasadena

Waterfront | Pool, Dock & Sleeps 12

Your private waterfront escape. Dive into the pool, fish off the dock, or watch the sunset over the Chesapeake Bay. This 5-bedroom Pasadena home sleeps 12 and has everything your group needs: a fully equipped kitchen, BBQ grill, spacious living areas upstairs and down, and direct water access. The 270-degree sunroom is the best seat in the house. Perfect for family reunions, friend getaways, or anyone who wants a real Maryland summer. 30 minutes to Annapolis, 20 to Baltimore.

LocationFamilySleep quality

4.93 out of 5 average rating, 44 reviews

Top guest favourite

Guest house in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

ValueFamilyAccuracy

5.0 out of 5 average rating, 229 reviews

Guest favourite

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

Waterfront Cheerful 5 home

Welcome to this brand-new waterfront retreat featuring a private 80ft pier, perfect for family reunions, vacations, or group getaways. This spacious home offers 5 bedrooms and 4 bathrooms (one bedroom on the main level and four upstairs), plus an expansive custom kitchen. Conveniently located just 11 miles from BWI Airport, 12 miles from downtown Baltimore, 17 miles from the Naval Academy in Annapolis, and 40 miles from Washington, D.C.

ValueFamilyParks

4.94 out of 5 average rating, 184 reviews

Top guest favourite

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

Place to stay in Glen Burnie

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

FamilyLocationAmenities

4.94 out of 5 average rating, 416 reviews

Top guest favourite

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Kick back at this cheerful waterfront escape on Thompson Creek—a favorite for families & wedding guests! With easy, local access to eight nearby venues, it’s the perfect home base. Enjoy sunsets, boating, and all Kent Island adventures. Thompson Creek leads to the Chesapeake Bay, with Annapolis, Kent Narrows, and St. Michaels close by. Relax on the screened‑in porch, and enjoy a remote feel with shops minutes away.

FamilyLocationKitchen

4.99 out of 5 average rating, 154 reviews

Superhost

A wooden dock extends into the water, equipped with boat slips on either side. Lush green grass frames the foreground, while calm waves ripple in the background. The scene is set under a soft, cloudy sky, providing a serene waterfront view.

Home in Pasadena

Beautiful Waterfront Home With Theater Room

This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!

FamilyLocationNearby

4.86 out of 5 average rating, 132 reviews