Vacation rentals in Chester

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!

Boho River Cottage

A Chesapeake Bay getaway located on the North East River. The renovated cottage sleeps 4 people. Nap in our 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 & mountain biking. Visit historic Havre de Grace, Hollywood Casino, or relax and catch a sunset and the cool breeze coming off the North East River

Bright and airy townhome with outdoor seating

This beautiful end unit townhouse with natural sunlight in every room. Enjoy the airy atmosphere with plenty of room to entertain but quiet enough to relax and get away. 5 Minutes from a variety of restaurants, University of Delaware, close to major highways, and best of all only 15 minutes from tax-free shopping mall in Delaware!!! Highlights: Two spacious bedrooms with full ensuites, deck right off the living room, desk by the large bay windows. Fully fenced in back yard for furry friends.

Center City: Safe, Private, Walkable!

Beware of unlicensed AIRBNBs! This one is Philly-approved! LITERALLY THE CENTER OF IT ALL. LOCATION! LOCATION! LOCATION! Permit Number ZP-2021-008507 Newly-remodeled room, registered Historic Landmark home in Center City (12th & Pine) with private entry (no shared entrance to your space). Private bathroom (Stall shower/vanity), twin bed, and desk. Ideal for lone traveler. Very small, perfect for on-the-go person. Mini-fridge. Microwave. AppleTV. Keurig. WiFi. No kitchen. No washer/dryer.

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

King size bed condo all cherry wood cabinets/floor

You'll have a great time at this comfortable place to stay plus its very private no one will even know where you are it's a little hideaway, Real secrets are kept here stay here and never leaves. this place is steamed after every visit and clean from top to bottom unlike some hotels that Rush just to get the other guest in. It's always been two guest but as of lately most people want to bring an extra person so I add three however if booking for 3 the 3rd person have to take the couch.

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.

Beautiful 1 Bedroom in the Heart of Chestnut Hill

Welcome to our quiet, lately renovated apartment just steps from historic Germantown Avenue in the heart of Chestnut Hill. This charming neighborhood offers a perfect blend of tranquility and convenience, with Pastorius Park and all the local shops, cafes, and attractions. The apartment features a spacious, open floor plan with a fully equipped kitchen, a cozy living area, a restful bedroom, and a private entrance—all designed to make you feel right at home.

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.