Vacation rentals in Bear

Serene Lake House with private pool and views!

Welcome to your very own Lakeside paradise! Picturesque enough to feel like a real getaway, but cozy just like home. Featuring a private pristine, heated swimming pool (open May 15-Sep 14), a 6 person hot tub (open Sep 17-May tbd) and stunning views, you will not be disappointed! Tons of room to spread out: huge living room with fireplace, screened-in porch, two outdoor fire pits, and several sitting areas. There are plenty of ways to relax and unwind. Enjoy your next getaway at Sunset Lagoon!

Small Town Vibes

Relax during your stay in a fully remodeled town home in the center of Small Town Rising Sun MD! There is so much to offer with the location and renovations of this town home… Local coffee shops, Grocery Store and restaurants in walking distance to quaint historical downtown Main Street. Also many actives are in the area like Ripken Stadium, an art studio and so much more! WiFi and basic necessity’s will always be included during your stay. We welcome you to come stay and relax while visiting!

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

The Loft at Jackson Farm-Your Relaxing Destination

The Loft at Jackson Farm- Come experience the hospitality that so many 5 Star reviews talk about! This luxury loft apartment is your next relaxing getaway! It features spectacular views of Amish farmland. Built with old world craftsmanship, from the field stone walls to the walnut counters. While this property is private and secluded, we are close to many of Lancaster and Chester Counties abundant attractions. Shopping, Hiking, Entertainment, and Restaurants are all in the local area.

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!

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.

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.

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.

Syd Acres

Unplugged retreat. Great for birders, piano players, gardening fans, antiquers. Twenty minutes from historic Havre de Grace. Nearby gardens include: Longwood Gardens; Chanticleer Garden; Winterthur Museum, Garden, and Library; and LaDew Topiary Gardens. Small kitchen with microwave, sink, fridge, and coffee maker. Private entrance. Smoke detectors, hair dryer. No WiFi. No stove.