House holiday rentals in Chesapeake City

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Top-rated house rentals in Chesapeake City

Guests agree: These houses are highly rated for location, cleanliness and more.

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Guest favourite

Home in Timonium

4.96 out of 5 average rating, 238 reviews

* Gorgeous New House w/ Luxury, Charm, & Comfort *

Imagine having your entire family or friends together all under the same roof enjoying a beautifully decorated, brand new house with loads of amenities. Well, imagine no more!!!! This home has it all – 4 beds (3 king / 1 queen) with plush mattresses & high end bedding & 2 baths, 3 smart TVs, washer/dryer closet, open living space w/ 20 ft ceilings leading to farmhouse style kitchen full of functionality & style, and awesome deck w/ sectional couch, mounted TV, montrous picnic table, & 2 heaters.

Top Guest favourite

Home in Rock Hall

5 out of 5 average rating, 35 reviews

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

Top Guest favourite

Home in Rock Hall

5 out of 5 average rating, 86 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Top Guest favourite

Home in Hampden

4.97 out of 5 average rating, 154 reviews

Full house in “coolest neighborhood in America”

Small but cozy single family in Northern Baltimore, located in the very sought after Hampden neighborhood. 5 minute walk to “the Avenue” and 34th Street lights at Xmas. Directly across the street is a Walgreen’s, MOM’s Organic Market, gym, restaurants, UPS Store, etc. A private driveway, manicured back yard w/ hardscape, fire pit and tons of indoor amenities offer a convenient and relaxing stay in this quaint Baltimore hood. Cleaned by COVID-trained professionals after each reservation.

Guest favourite

Home in Wilmington

4.93 out of 5 average rating, 122 reviews

Five Star Accommodations

We've had more than one guest tell us that Bancroft Cottage was better than their stay at the Hotel Dupont! (and a lot more reasonable may we add). In the event that we already have a guest checking out on the day you are checking in, or checking in on the day you are checking out we will need to adjust the check-in or check-out time by one hour to allow sufficient time for the Housekeeper. We have exterior cameras in the front and back for added security for our guests and the property.

Guest favourite

Home in Frederica

4.92 out of 5 average rating, 323 reviews

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

Top Guest favourite

Home in Chestertown

5 out of 5 average rating, 192 reviews

Totally Renovated historic house near town center

Renovated 19th century home. 3 king beds, 2 queens. 55” TV in family room, 2 more. 1st floor bedroom with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 more bedrooms with queens. 1 loft connected to a 2nd story bedroom with 2 twins. Fenced yard and an acre of private gardens. Fire pit. New Weber grill

Top Guest favourite

Home in Perryville

4.99 out of 5 average rating, 115 reviews

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!

Superhost

Home in Annapolis

4.85 out of 5 average rating, 221 reviews

Spacious Home in Private Neighborhood with Beach

A beautiful and spacious home located on the Severn River in the gated community of Epping Forest! The house is just 7 miles from downtown Annapolis and offers guests a private, secluded home away from home. A private beach and club house are located within walking distance! Enjoy a fire on either of the two levels of private decks, or gather around the large dining room table for any of the provided board games. An abundance of amenities will make your stay more than comfortable!

Guest favourite

Home in Elkton

4.84 out of 5 average rating, 360 reviews

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.

Guest favourite

Home in Perryville

4.93 out of 5 average rating, 214 reviews

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Guest favourite

Home in Pasadena

4.89 out of 5 average rating, 101 reviews

Beautiful Waterfront Home With Theater Room

This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!