Vacation rentals in Stewartstown

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Top-rated vacation rentals in Stewartstown

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Guest favorite

An outdoor seating area is set on a wooden deck, featuring a large table surrounded by light blue chairs. A fire pit is visible in the foreground, with lush greenery and a sandy beach in the background, along with the home and upper deck partially shown.

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Top guest favorite

A tranquil view of a sandy beach along a calm river, framed by green grass and gentle waves lapping at the shore. The scene is dotted with trees and overlooks a distant white house, creating a serene atmosphere.

Cottage in Charlestown

4.98 out of 5 average rating, 101 reviews

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

Guest favorite

A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Guest favorite

Home in Mechanicsburg

4.92 out of 5 average rating, 12 reviews

Modern Creek View Cabin Loft Free Kayaks Fire Pit

Gather & relax at this modern Cabin by the Conodoguinet Creek. Loft bedroom w/ king size bed, queen size bedroom, and bunk house bedroom. 3 total bedrooms. Full Kitchen w/dishwasher, Keurig, Reverse osmosis water system. Peaceful getaway surrounded by nature yet close to food & shopping. Deck balcony Creek front picnic table, grill and firepit across the quiet road out front of cabin. Perfect for families, little gatherings, couples, or a solo retreat spot. 4 Kayaks free for guests!

Guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Guest favorite

A game room features a variety of entertainment options, including arcade machines and a shuffleboard table. A vending machine is also present, providing snacks and drinks. The room is designed with colorful accents and a green carpet area, making it inviting for guests of all ages.

Home in Hummelstown

4.93 out of 5 average rating, 128 reviews

Small Town Sweets: Charming Home Near Hersheypark

Beautifully restored home(2019) in Hummelstown, PA, about 3 miles from Hersheypark. Walking distance to many local restaurants, bars, & shops. Game room on 1st level will keep kids and teens entertained. Three large BRs with Queen beds, and 1 Kids' bedroom that sleeps 4, all of which include a smart TV. Queen rooms include luggage bench, full length mirror, and USB charging ports. New appliances, furniture, and bedding throughout. Oversized living space and front porch.

Guest favorite

The outdoor deck is lined with string lights, providing a warm ambiance against a stunning sunset backdrop. A hot tub is located to the left, with comfortable seating available for relaxation. Views of rolling fields and a serene landscape can be seen in the distance.

Home in Gap

4.9 out of 5 average rating, 135 reviews

Dream View

Welcome to our beautiful 3 bedroom,2 bath home with an attached 1 bedroom,1 bath apartment that’s perfect for families or groups who value privacy and convenience. Enjoy breathtaking views of the picturesque surroundings right from the comfort of your home or bask in the serene atmosphere of the big backyard where you will possibly see wildlife. The hot tub is an added bonus,perfect for a relaxing evening under the stars.

Top guest favorite

A quiet garden area features a stone pathway winding through vibrant greenery and blooming plants. The pathway is bordered by large shrubs and trees, creating a serene natural setting. A blue garden sign stands prominently among the foliage, adding a touch of color.

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Guest favorite

Home in East Earl

4.88 out of 5 average rating, 123 reviews

Cottage On Main-cozy 3/1.5 near Shady Maple

Escape to this peaceful haven surrounded by picturesque Amish farmland. This 3-bedroom, 1.5-bath retreat is thoughtfully designed to make you feel at home. Cook in the fully stocked kitchen or savor local takeout. Start your day with coffee on the front porch, observing the charming buggies passing by. Experience serenity and comfort in this idyllic rental, perfect for a relaxing family getaway.

Top guest favorite

Condo in Betterton

5 out of 5 average rating, 16 reviews

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Top guest favorite

Cottage in Wrightsville

4.95 out of 5 average rating, 116 reviews

-The Pool Cottage at The Roundtop Estate-

Want a Unique Getaway!! with a Hot Tub/Fireplace, and Espresso Machine! Where to start? From the architecture to the luxury furnishings, to the woods surrounding it, to the hot tub, to the Gas burning fireplace to sit beside your loved ones while drinking your latte that you can make by using the espresso machine, An oasis!

Guest favorite

A wooden pier extends into calm waters, accommodating a boat. Cozy seating areas, including lounge chairs and a shaded table, are positioned on the sandy beach. Lush trees line the waterfront, providing a scenic backdrop.

Home in Essex

4.81 out of 5 average rating, 78 reviews

Sunset Haven on Sue Creek

Unparalleled Sunsets on the Water! This unique simple renovated cottage, offers an amazing waterfront experience with a private sandy beach, amazing nightly sunsets and a 60 foot pier which can hold most vessels up to 45 feet. Owners are very friendly live next door and are happy to help make your relaxation complete.