Vacation rentals with a washer and dryer in Kent County

4.97 out of 5 average rating, 230 reviews

Apartment in Chestertown

Private cozy cottage - center of Chestertown .

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), two 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.

5 out of 5 average rating, 86 reviews

An aerial view showcases a quiet neighborhood with residential homes and proximity to the Chesapeake Bay. The large backyard is visible, along with a mix of greenery and pavements. Multiple marinas are located nearby, complementing the tranquil setting.

Home in Rock Hall

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)

A well-lit hallway leads to an inviting living space. Light-colored walls enhance the airy feel, while a cozy couch is visible through the doorway. Natural light enters from a window, and a textured rug adds warmth to the floor, creating a welcoming environment.

4.95 out of 5 average rating, 21 reviews

Charming Haven on High

Featuring an open, updated kitchen, 2 bedrooms, 1.5 bathrooms for up to 4 guests. Explore historic downtown with unique shops, delightful dining options, & the Arts & Entertainment district that stretches to the Chester River, just a 5-min. walk. Numerous events, include the Tea Party Festival, Summer Concert Series, First Fridays, Downrigging Weekend, the Annual Dickens of a Christmas & Saturday morning Farmers Market. Steps from Washington College, it’s ideal for parents & alum visiting.

A screened-in porch features a wooden dining table surrounded by woven chairs. Natural light filters through the open sides, illuminating a patterned area rug. Trees are visible in the background, enhancing the serene outdoor atmosphere.

4.97 out of 5 average rating, 119 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

4.99 out of 5 average rating, 108 reviews

Cottage in Rock Hall

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Casa particular in Chestertown

An inground pool is surrounded by brick paving, with several lounge chairs positioned nearby. The pool's turquoise water is partially shaded by a large tree, providing a serene outdoor setting. Lush green grass and a wrought-iron fence are visible in the background.

4.92 out of 5 average rating, 143 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!

4.9 out of 5 average rating, 78 reviews

The image displays a charming row of houses with front porches framed by lush greenery and flowering plants. Steps lead up to the porches, inviting entryways provide seating areas, and a paved walkway runs parallel to the homes.

Apartment in Chestertown

1-br apt in downtown Chestertown (Unit 1)

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

4.98 out of 5 average rating, 88 reviews

A bright open living space features large windows allowing natural light to fill the room. Comfortable seating is arranged around a glass coffee table. The dining area is visible in the background, with a wooden table and chairs, connecting to a modern kitchen with stylish cabinetry.

Apartment in Chestertown

Bright, new apartment in the heart of Chestertown

Flooded with light and in the center of all Chestertown has to offer. Have a front seat to Chestertown’s festivals. The apartment spans the entire front of the second floor of the recently restored building, built in 1877. Open living room/dining area/kitchen. Historic character with all modem conveniences, including dishwasher, washer/dryer, Smart TV and high speed wifi internet access. Off-street parking for one car on first come first served basis with ample street parking.

5 out of 5 average rating, 12 reviews

A charming brick townhouse features large windows adorned with blue shutters and a welcoming entrance. The building showcases a classic architectural style, complemented by potted plants at the base and an American flag hanging beside the front door.

Townhouse in Chestertown

The Retreat in Historic Downtown Chestertown

Located in charming historic Chestertown, this townhouse feels like a city brown stone with gorgeous brick throughout and exquisite bathrooms. Newly remodeled, this home feels cozy, yet indulgent. Centrally located with the most delicious bakery a few feet away, the best restaurants a block away, and Washington College a mile away! This three story gorgeous property built in 1870 is in the absolute best location surrounded by the rich history and beauty of this special town.

A modern kitchen is displayed with white cabinetry and stainless steel appliances. A central island features a black tabletop with four high-backed woven chairs. Light wood flooring enhances the spacious feel, complemented by a sliding glass door providing access to the backyard.

5 out of 5 average rating, 38 reviews

NEW Chestertown Retreat

Enjoy this newly built (July 2023) semi-detached home with new furnishings, fully stocked with everything you need and private fenced back yard. Located less than 1/2 mile to Washington College and 1.5 miles to downtown, this home is close to everything Chestertown has to offer. Perfect for parents and families visiting students, hunting trips, weddings or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

The exterior of a newly remodeled Victorian house is shown, featuring a two-story structure with a green metal roof. The front porch is adorned with a decorative railing, and large glass doors provide access to the welcoming outdoor deck, which is lined with wooden flooring.

4.95 out of 5 average rating, 116 reviews

Classic Victorian in Chestertown

A delightful hideaway all to yourself! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Plenty of on-street parking. Professional cleaning before every visit (alcohol and/or bleach solution), combined with complete ventilation of the house 24 hours ahead of arrival.