Vacation rentals in Jarrettsville

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Top-rated vacation rentals in Jarrettsville

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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

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

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 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.

Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 154 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Top guest favorite

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

4.98 out of 5 average rating, 102 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

A private outdoor space is highlighted by a hot tub, surrounded by a wooden fence for added privacy. Nearby, a comfortable seating area features a gray sofa, complemented by greenery and decorative plants, creating an inviting setting for relaxation.

Apartment in Leola

4.98 out of 5 average rating, 59 reviews

Dreamwood on main w/ hot tub + toy room for kids

Make memories with your whole family at this beautiful cozy place . You are at a convenient location right along Main Street (Route 23 ) with lots of places to visit near by . Our patio has a grill, a hot tub, and picnic table with extra seating , a perfect place for a relaxing evening outside . Our fully functioning kitchen will make cooking meals easy . And the basement has a kids play area and a foosball table . We hope you might enjoy the space as much as our family does .

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

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 clean, modern bathroom is presented with a glass shower enclosure and a white marble countertop. Black and white tiled flooring creates a classic look. Natural light enters through a window, enhancing the space's brightness.

Guesthouse in Arnold

4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

Immaculately designed separate guest suite/apartment in separate building with private entrance, private bath, Queen bed and gorgeous water views from every window. Guests have their own refrigerator, coffee maker and microwave and convection oven and air fryer, Xfinity tv 43" and high speed 5G internet for guests. Up to 2 guests can dine in the apartment or enjoy outdoor deck dining overlooking Lake Placid.

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

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

5 out of 5 average rating, 18 reviews

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.

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.