Holiday rentals in Street

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Top-rated holiday rentals in Street

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

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Guest favourite

Home in Middle River

4.97 out of 5 average rating, 35 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.

Guest favourite

Cottage in New Holland

4.99 out of 5 average rating, 148 reviews

Exquisite cottage with valley views and Hot Tub

Come stay at our fully renovated cottage. Brand new hot tub just installed Dec 2024 We just finished a full house remodel in 2022 If you are looking for the perfect place to relax and unwind this house is for you. It has scenic valley views and a large private backyard, but is still within 30 minutes of the best lancaster county has to offer including Sight and Sound, Dutch Wonderland, American music theater and Strasburg railroad. Also within minutes of Shady Maple Smorgasboard and Intercourse.

Guest favourite

Home in Lutherville-Timonium

4.91 out of 5 average rating, 163 reviews

* 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!

Guest favourite

Flat in Leacock-Leola-Bareville

5 out of 5 average rating, 43 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 favourite

Cottage in Pasadena

4.97 out of 5 average rating, 171 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.

Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 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!

Superhost

Cottage in Pasadena

4.82 out of 5 average rating, 17 reviews

Sunset Lagoon Home

Have fun with the whole family at this stylish place! Our cozy cottage sits at the edge of a beautiful creek. Peaceful and tranquil, yet close to shops and restaurants, this waterfront property is perfect for serene getaways and family gatherings! Everyone will enjoy a unique and private space to relax. From peaceful mornings lounging on the balconies, to afternoons filled with fishing to magical sunsets on the 110-foot pier, this setting will quickly become a family favorite!

Guest favourite

Home in Gap

4.91 out of 5 average rating, 120 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 favourite

Guest house in Owings Mills

4.97 out of 5 average rating, 114 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 favourite

Home in East Earl

4.89 out of 5 average rating, 107 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.

Guest favourite

Flat in Betterton

5 out of 5 average rating, 15 reviews

Bayside Bungalow

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 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.

Guest favourite

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.