Vacation rentals in Woodlyn

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woodlyn

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

Cottage in North East

5 out of 5 average rating, 29 reviews

Charming Waterfront Cottage w Private Boat Dock

Welcome to The Dabbling Duck! Located on the beautiful North East River, this waterfront cottage is a little slice of Chesapeake paradise. Guests have access to a private dock for boating, fishing, paddle sports, or relaxing to picturesque surroundings. Hiking, biking, and wildlife enthusiasts love the close proximity to over 5,000 acres of pristine nature. For the traveler in search of antiques, delicious eastern shore fare, or live music, Main Street and Nauti Goose are only a short walk away.

Top guest favorite

A welcoming living area features exposed wooden beams and a cozy sofa adorned with cushions. A light-colored coffee table sits atop a textured rug, while a colorful floral accent wall adds a pop of color. Soft lighting creates a relaxed ambiance throughout the space.

Apartment in Chesapeake City

5 out of 5 average rating, 16 reviews

The Pearl: a 70s vibe, hip/cozy

The Pearl is located in the heart of historic Chesapeake City; just steps from all the boutiques, restaurants & nightlife with a lovely view of the C&D Canal. It's cozy, but functional with 2 workspaces, 2 bedrooms & all the amenities you'd want in your home away! We provide a Nespresso machine & excellent coffee, snacks, sparkling water, full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! It's not your usual Victorian spot. Come stay with us, you won't regret it!

Top guest favorite

A modern kitchen features light wooden cabinetry and open shelving. The stainless-steel appliances are complemented by a large island with bar seating. Natural light floods in from nearby windows, illuminating the workspace, while decorative plants add a touch of greenery.

Home in North East

4.96 out of 5 average rating, 46 reviews

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people. Nap in our secluded backyard gardens. The cottage includes water access, kayaks, bikes, and a SUP board. Explore the town of NE to shop and dine in the region's top restaurants. Minutes from Elk Neck State Park which offers hiking, fishing, bird watching & mountain biking. Visit historic Havre de Grace, Hollywood Casino, or relax and catch a sunset and the cool breeze coming off the North East River

Guest favorite

A modern kitchen features a central island with bar seating for three. Light fixtures illuminate the space, highlighting white cabinets and stainless steel appliances. A countertop with a subtle pattern complements the tiled floor, while decorative items are arranged on the island.

Townhouse in Elkton

4.92 out of 5 average rating, 61 reviews

Bright and airy townhome with outdoor seating

This beautiful end unit townhouse with natural sunlight in every room. Enjoy the airy atmosphere with plenty of room to entertain but quiet enough to relax and get away. 5 Minutes from a variety of restaurants, University of Delaware, close to major highways, and best of all only 15 minutes from tax-free shopping mall in Delaware!!! Highlights: Two spacious bedrooms with full ensuites, deck right off the living room, desk by the large bay windows. Fully fenced in back yard for furry friends.

Guest favorite

The entrance door features intricate glass panels and a dark wood finish, welcoming guests with a sense of entry. Adjacent to the doorway, a glass door leads to a bright interior space, showcasing a light-colored dining area with modern furnishings.

Apartment in Bryn Mawr

4.93 out of 5 average rating, 258 reviews

+Restaurants Coffee Colleges+ Bryn Mawr Has It All

Welcome to Bryn Mawr, Pennsylvania! This comfortable 2nd floor apartment layout is cozy whether you are by yourself or in town with a large family of 7. It has an eat in kitchen for enjoying takeout or preparing a meal yourself. Each back bedroom comfortably fits 2 people for sleeping, the front br has a single bed, and the living room sofa doubles as a pull out couch. With ROKU on the TV you have an instant entertainment center. Wake up to free hot coffee prepared in the Keurig coffee maker.

Guest favorite

The image depicts a historic brownstone with a red brick facade. Steps lead to a black front door, flanked by windows adorned with flower boxes. A street sign indicating 'LEFT LANE MUST TURN LEFT' is visible beside the entrance, along with a glimpse of neighboring buildings.

Guest suite in Center City

4.92 out of 5 average rating, 418 reviews

Center City: Safe, Private, Walkable!

Beware of unlicensed AIRBNBs! This one is Philly-approved! LITERALLY THE CENTER OF IT ALL. LOCATION! LOCATION! LOCATION! Permit Number ZP-2021-008507 Newly-remodeled room, registered Historic Landmark home in Center City (12th & Pine) with private entry (no shared entrance to your space). Private bathroom (Stall shower/vanity), twin bed, and desk. Ideal for lone traveler. Very small, perfect for on-the-go person. Mini-fridge. Microwave. AppleTV. Keurig. WiFi. No kitchen. No washer/dryer.

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

Top guest favorite

Two wooden lounge chairs are positioned facing a serene waterfront view. A fire pit sits in the center of a grassy area, surrounded by the gentle slope leading to the water's edge. The calm water extends toward distant hills under a clear blue sky.

Home in Perryville

4.99 out of 5 average rating, 115 reviews

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Guest favorite

The entrance to Fairwinds Cottage is highlighted by a white bench placed in front of a blue door. The cottage's exterior is adorned with vibrant flowering plants in window boxes, enhancing the welcoming atmosphere.

Guesthouse in Chesapeake City

5 out of 5 average rating, 163 reviews

High-End Cottage, Water View, Chesapeake City, MD

"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.

Guest favorite

An outdoor patio area is showcased, featuring a combination of seating arrangements. A large umbrella shades a dining table surrounded by chairs, while a sectional sofa with soft cushions is accompanied by decorative poufs. String lights are suspended overhead, enhancing the relaxing atmosphere.

Home in Elkton

4.84 out of 5 average rating, 360 reviews

Cozy Cottage Elkton North East 3bed 2 bath Patio

Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark & UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio t w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc.

Superhost

A sunlit sitting area features a wooden bench with a comfortable cushion, accompanied by a modern lamp on a small table. Nearby, a wooden shelf offers storage and decor. Large windows allow natural light to brighten the space, with a view of greenery outside.

Apartment in Chestnut Hill

4.77 out of 5 average rating, 206 reviews

Beautiful 1 Bedroom in the Heart of Chestnut Hill

Welcome to our quiet, lately renovated apartment just steps from historic Germantown Avenue in the heart of Chestnut Hill. This charming neighborhood offers a perfect blend of tranquility and convenience, with Pastorius Park and all the local shops, cafes, and attractions. The apartment features a spacious, open floor plan with a fully equipped kitchen, a cozy living area, a restful bedroom, and a private entrance—all designed to make you feel right at home.

Guest favorite

A serene aerial view captures the retreat center nestled by the water, surrounded by lush greenery. Soft hues of purple and pink fill the sky at sunset, reflecting on the calm bay waters. A long pier extends into the water, offering a tranquil point of access.

Tiny home in North East

4.73 out of 5 average rating, 86 reviews

Cozy Log Cabin on the Bay at Sandy Cove

Tiny Home Nestled in the woods, this 600 sq ft, Conestoga Log Cabin is cozy & rustic, yet meets all of your needs. Sleeps 6-8 - Bedroom w/ a double bed - Bedroom w/ bunk beds - Open loft w/ 2 single beds - Living area with a futon - Kitchenette - Dining area - WiFi and a smart TV Stunning Location Sandy Cove is a Christian retreat center with 200+ acres on the headwaters of the Chesapeake Bay, offering beautiful views in all seasons.