Vacation rentals in Perryville

4.95 out of 5 average rating, 39 reviews

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

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.

4.96 out of 5 average rating, 46 reviews

The cottage's exterior features a welcoming façade with a green color scheme. A compass motif sits above the entrance. Surrounding gardens include various plants and shrubs, with a stone pathway leading to the front door. Large windows allow natural light into the space.

Home in North East

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people with 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, and mountain biking. Visit the lighthouse, Havre de Grace, Hollywood Casino, or relax & catch a sunset with a cool breeze coming off the North East River.

4.92 out of 5 average rating, 191 reviews

A modern kitchen featuring sleek black and white cabinetry, stainless steel appliances, and a minimalist design. The space includes a gas stove, a microwave, and a refrigerator. Natural light comes in through a window, illuminating the wood-like flooring and nearby staircase.

Home in Timonium

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

4.98 out of 5 average rating, 102 reviews

The cottage showcases a dark blue exterior with white shutters, set against a lush green yard. A patio area is visible, featuring assorted seating options, including red and black chairs. Tall trees provide natural shade, enhancing the outdoor space.

Cottage in Charlestown

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

4.97 out of 5 average rating, 172 reviews

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

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.

4.88 out of 5 average rating, 124 reviews

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

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!

5 out of 5 average rating, 29 reviews

The charming cottage features a covered front porch with a white railing and a decorative door, framed by lush greenery and blooming hydrangeas. A flag is displayed proudly, while stairs lead up to the welcoming entrance. Natural light brightens the overall exterior.

Cottage in Betterton

Charming Home w/Great Porch

We would love to share our well-loved cottage on the Bay with you. Most loved for its beautiful views and quiet town, it is a perfect place to relax with great beach access. We think you'll love it too. Plenty of space to spread out and comfy spaces to enjoy together: whether on the screened porch (our favorite), in the updated foodie-kitchen, or swinging on the swing, snoozing in hammock or walking to the beach - you will be glad you found this place-we definitely are!

4.9 out of 5 average rating, 136 reviews

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

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.

Guesthouse in Owings Mills

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.

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.

5 out of 5 average rating, 16 reviews

Condo in Betterton

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.

5 out of 5 average rating, 18 reviews

The entrance of the home is framed by a covered porch with wooden support beams. A pair of rocking chairs are positioned on the porch, while colorful flower beds with seasonal blooms enhance the inviting atmosphere. The front door is decorated with a welcome sign.

Home in North East

Heron Creek- Historic home on Main Street

Beautiful home located in the heart of downtown. This 3 full bath/3 bedroom was recently renovated. Original hardwood floors throughout. This is an older home with narrow steps. It offers off street parking & is walkable to shops, restaurants, water sports & bike rentals. Close to Turkey Point Lighthouse, the park, fishing, boating & hiking.

4.81 out of 5 average rating, 78 reviews

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

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.

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Stay near Perryville's top sights

Johnny's Sushi House10 locals recommend

The Vineyard Wine Bar6 locals recommend

Coakley's Pub5 locals recommend

Perryville Marc station3 locals recommend

Havre De Grace Marina3 locals recommend

Cultural Center at the Opera House3 locals recommend

Other great vacation rentals in Perryville

4.89 out of 5 average rating, 38 reviews

Home in Charlestown

The Sunset House

4.96 out of 5 average rating, 56 reviews

The kitchen is designed with modern white cabinetry and natural wood accents. New appliances include a refrigerator, stove, and dishwasher. A central island with seating is complemented by large windows, allowing ample natural light to brighten the space.

Home in Quarryville

Charming 3-Bed Single Level Cottage

4.93 out of 5 average rating, 90 reviews

A covered outdoor seating area features four cushioned chairs with red accents, arranged around a small side table. Potted flowers add color to the space, while a lush green landscape is visible in the background, enhancing the peaceful atmosphere of the setting.

Home in Paradise

Paradise Lancaster Vacation Home central location!

4.91 out of 5 average rating, 11 reviews

A spacious outdoor area features a gazebo with a red umbrella and a table surrounded by chairs. A grill is positioned nearby on a lush green lawn, framed by trees in a serene natural setting.

Home in New Providence

The Cottage at French Country Manor

4.86 out of 5 average rating, 58 reviews

A spacious living area features a large sectional sofa positioned around a coffee table, with a geometric area rug beneath. A flat-screen TV is mounted on the wall, and natural light streams in through large windows, enhancing the open layout that flows to the dining area.

Home in Pasadena

Beautiful Home Near Beach and Patapsco River

4.96 out of 5 average rating, 136 reviews

The kitchen features exposed brick walls and open wooden shelving, exhibiting various kitchenware. A stainless steel stove is complemented by a large farmhouse sink and modern faucet. Light wood countertops provide a warm contrast to the cabinetry, creating a functional and inviting cooking space.

Townhouse in Fells Point

Artsy, Historic Rowhouse with Striking Harbor Views

4.92 out of 5 average rating, 12 reviews

A gentle stream meanders through a wooded area, with smooth rocks lining its banks. Water flows over small cascades, surrounded by a mix of bare trees and moss-covered stones, creating a serene natural landscape.

Cabin in Airville

AFrame Cabin at Mill Creek