Chesapeake City vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake City

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Yurt in Elkton

5.0 out of 5 average rating, 105 reviews

Creekside Forest Nature Retreat : Mongolian Yurt

Wake up to birds singing! Enjoy 55 private, peaceful acres with abundant forest wildlife. Hawks, owls, deer and more! Our Mongolian-style yurt is 200 sq. feet with a full bed, solar shower(summer), pop-up private flushing poddie, hammock, fan, lights, wood stove (winter), grill and fire pit. Optional packages include, Farm to table Cornish hen dinner delivered ($39), S'mores $12, extra firewood ($10), one hour farm tour ($40) which includes feeding cows, holding chickens and visiting our apiary.

Dec 5 – 12

G$25,007 GYD per night

Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 110 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Jun 12 – 19

G$21,365 GYD per night

Guest favorite

Guest suite in Newark

4.99 out of 5 average rating, 169 reviews

Spacious, light filled studio 2 blocks from UDel

Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, only a few minutes' walk to the center of downtown Newark. Newark is a thriving college town with restaurants, history museum, library, small stores erc. The studio is in a quiet, friendly, safe, historic and walkable neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

May 5 – 10

G$23,419 GYD per night

Guest favorite

Apartment in Havre de Grace

5.0 out of 5 average rating, 100 reviews

Retro Downtown One Bedroom at JoRetro

Indulge in a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four meticulously decorated units, each inspired by an iconic Pyrex design. Relax on the queen-size bed, with luxury linens, and enjoy retro and vintage items, including Butterprint Pyrex pieces. Explore a variety of restaurants and unique shops, all within walking distance. Don't miss the opportunity to visit the historic Lighthouse and museums.

Aug 12 – 19

G$27,260 GYD per night

Guest favorite

Guesthouse in Quarryville

4.99 out of 5 average rating, 231 reviews

The Olde Wash House on Camargo

Come and relax in our newly remodeled, cozy, cottage style home with it's own private entrance, surrounded by working Amish farms, just outside of town. A short 15 minute drive to Historic Strasburg, Sight and Sound Theater, Antique Shopping, Tangor Outlets and more! Hiking Trails close by include Enola Grade Trail, Pinnacle Point, Muddy Run Park, and Sickman's Mill. If golfing is your desire, Tanglewood Golf Club is just 10 minutes away. We hope you enjoy your stay!

Feb 7 – 14

G$20,311 GYD per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Oct 1 – 8

G$29,274 GYD per night

Guest favorite

Guesthouse in Chesapeake City

5.0 out of 5 average rating, 149 reviews

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.

Jun 30 – Jul 7

G$49,104 GYD per night

Guest favorite

Cottage in North East

4.97 out of 5 average rating, 438 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

Mar 18 – 25

G$23,080 GYD per night

Guest favorite

Guest suite in Newark

4.99 out of 5 average rating, 155 reviews

Private apartment & floor, 200 yds from UD center

1 block to UD center, 0.5 mi to the bustling City of Newark center and to Amtrak. 1 King, 2 Queen, 1 Twin. You’ll love the location and privacy. Good for couples, adventurers, business travelers, and UD families. Friendly hosts, but you'll have the whole floor to yourself and won't see us! Separate entrance to a finished lower level suite w/ King bedroom, wet bar & fridge, and additional common area beds if more than 2 people. Use the back yard and patio, too!

Apr 25 – May 2

G$30,207 GYD per night

Guest favorite

Cottage in North East

4.94 out of 5 average rating, 279 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Jan 8 – 15

G$20,459 GYD per night

Guest favorite

Apartment in Rising Sun

4.97 out of 5 average rating, 197 reviews

Cross Keys Tavern

Built in 1744, this lovely home is the perfect country getaway. Cozy apartment in a historic property located in the little town of Calvert. Huge master bedroom with plenty of relax room. Private entrance with plenty of parking. Six miles from Fair Hill Natural Resources Area and a golf course practically in the back yard.

Oct 7 – 14

G$29,807 GYD per night

Guest favorite

Apartment in Chesapeake City

4.93 out of 5 average rating, 141 reviews

Bohemia Vista CC Horse Farm Apartment

Comfortable and private, 10 minutes from Chesapeake City This private apartment comes with a basic kitchen, private bedroom with king sized bed, common area twin bed, sitting area, bath with a jacuzzi tub, and expansive views of farmland and horses. Private entrance and use of private laundry room included.

Jul 28 – Aug 4

G$27,305 GYD per night