Vacation rentals in Kent County

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Top-rated vacation rentals in Kent County

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Guest favorite

Home in Chestertown

4.94 out of 5 average rating, 128 reviews

CHESAPEAKE SUNSETS

Escape to a quaint bayside cottage with sweeping views of the Chesapeake. Relax and enjoy beautiful sunsets from the bayside sundeck, screened porch or from the comfort of your home. Less than 2 miles to the seasonal Shanty Bar at Tolchester Marina featuring live music, dining and its own beach. One mile from a private community boat ramp to launch your water toys. 800 sq ft 2 bedroom 1 bath house is on Maryland’s Eastern Shore less than 2 hours from Washington, Baltimore and Philadelphia.

May 4 – 11

G$40,944 GYD per night

Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 193 reviews

Quiet, pet frienly, escape in center of town

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Dec 17 – 24

G$43,605 GYD per night

Superhost

Cottage in Betterton

4.79 out of 5 average rating, 52 reviews

Cottage By the Chesapeake

This cozy cottage on the Eastern Shore of Maryland sits on a spacious private lot a five minute walk to Betterton Beach! Relax on the screened-in porch or fully-furnished living room after a day in the woods, or cook a homemade dinner in our fully-equipped kitchen. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH! For a change of pace or a night out, Chestertown, Maryland is only a short drive away.

Jun 15 – 22

G$26,453 GYD per night

Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Nov 24 – Dec 1

G$64,306 GYD per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 131 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

Aug 13 – 20

G$34,693 GYD per night

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 102 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Dec 1 – 8

G$28,435 GYD per night

Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 68 reviews

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Jul 14 – 21

G$34,364 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.

Sep 13 – 20

G$29,096 GYD per night

Guest favorite

Guest suite in Joppatowne

5.0 out of 5 average rating, 83 reviews

Cozy, clean & spacious lower level of a new home

This is a spacious lower level of a newly built home. This private guest area has a lounge, dinning, and kitchenette in addition to a bedroom and a bathroom. Guests share only the main entrance of the townhouse with owners who live upstairs. This private decorated space includes a smart TV, comfortable seating, dining for 4, microwave, coffee maker, full refrigerator, toaster/air fryer, queen bed, wardrobe and dresser. Washer/dryer available upon request.

May 11 – 18

G$15,753 GYD per night

Guest favorite

Camper/RV in Chestertown

4.89 out of 5 average rating, 123 reviews

Cozy Airstream on a beautiful horse farm

You'll love this cozy 32' 1989 Airstream Excella 1000. It's got a comfy queen size bed in the bedroom and a couch that converts to a full size bed that could sleep another adult comfortably or a couple of kids. The farm is beautiful - you'll feel like you're on vacation. We have a fire pit out front and an 8' galvanized shallow trough pool in the summer. Complete with stove, fridge, microwave, gas grill and Keurig.

May 22 – 29

G$27,112 GYD per night

Guest favorite

Apartment in Rock Hall

4.96 out of 5 average rating, 47 reviews

Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

Dec 30 – Jan 6

G$29,804 GYD per night

Guest favorite

Guest suite in Chestertown

4.94 out of 5 average rating, 47 reviews

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Oct 16 – 23

G$34,483 GYD per night