Vacation rentals in Darlington

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Top-rated vacation rentals in Darlington

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Guest favorite

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

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

Home in Frederica

4.92 out of 5 average rating, 323 reviews

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

Guest favorite

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

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

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

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.

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

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.