Holiday 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!

+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.

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

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.

Historic Victorian just a block from the water!

*If you are in need of additional bedrooms or just more space, inquire about adding our 2Br/1Ba first floor unit to your rental* Welcome to Millard’s Rest! While retaining much of the original Victorian millwork and architecture, contemporary conveniences make this home a comfortable retreat for guests of all ages. Whether in town for a wedding, business trip, sports tournament, or just some R&R - "Millard's Rest" is a conveniently located home away from home!

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.

Little piece of paradise-Year round-Pet friendly

Looking for a relaxing getaway? Gandy's beach is the perfect place for you. This secluded beach is a perfect place to escape your everyday hustle and bustle. This 4 bedroom, 2 full bathroom house sits right on the water and sleeps up to 12. Feel free to bring your own fishing gear to fish right from the deck. We have 1 canoe and a few generic "orange" Life jackets to be used. If you have a jet ski or a boat you can drop it in at Sundog Marina.

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.