Holiday houses in Chester

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.

Charming Waterfront Cottage w Private Boat Dock

Welcome to The Dabbling Duck! Located on the beautiful North East River, this waterfront cottage is a little slice of Chesapeake paradise. Guests have access to a private dock for boating, fishing, paddle sports, or relaxing to picturesque surroundings. Hiking, biking, and wildlife enthusiasts love the close proximity to over 5,000 acres of pristine nature. For the traveler in search of antiques, delicious eastern shore fare, or live music, Main Street and Nauti Goose are only a short walk away.

The Pearl: a 70s vibe, hip/cozy

The Pearl is located in the heart of historic Chesapeake City; just steps from all the boutiques, restaurants & nightlife with a lovely view of the C&D Canal. It's cozy, but functional with 2 workspaces, 2 bedrooms & all the amenities you'd want in your home away! We provide a Nespresso machine & excellent coffee, snacks, sparkling water, full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! It's not your usual Victorian spot. Come stay with us, you won't regret it!

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!

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.

Discounted Stays | 2BR | Dog-Friendly | King | A/C

+Dog Friendly + 2 Miles to Marina + AC on site +Stocked Kitchen +1 Mi to Brewery, Sushi, Ice Cream & Other +2 minutes drive to kayaking, paddleboarding, outdoor rec +2 minute drive to fishing, Walking, Biking, Outdoor Rec at Marina +3 mile drive to Perryville park Prime location to hospitals, railroad travel, engineering firms, and numerous points of interest. If you like to fish or like walks along the water you need to stay here. SEE HOUSE RULES FOR DOGS.

Cozy Log Cabin on the Bay at Sandy Cove

Tiny Home Nestled in the woods, this 600 sq ft, Conestoga Log Cabin is cozy & rustic, yet meets all of your needs. Sleeps 6-8 - Bedroom w/ a double bed - Bedroom w/ bunk beds - Open loft w/ 2 single beds - Living area with a futon - Kitchenette - Dining area - WiFi and a smart TV Stunning Location Sandy Cove is a Christian retreat center with 200+ acres on the headwaters of the Chesapeake Bay, offering beautiful views in all seasons.

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.