Vacation rentals with a washer and dryer in Chestertown

4.95 out of 5 average rating, 152 reviews

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

4.89 out of 5 average rating, 140 reviews

The charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.

Cottage in Rock Hall

Cottage with Modern Updates - Walk to Waterfront!

Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

4.97 out of 5 average rating, 148 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.

4.88 out of 5 average rating, 113 reviews

The bedroom features a plush queen bed dressed in neutral linens, complemented by two bedside lamps and coastal-themed artwork. A cozy sitting area includes a light blue armchair and a small table. Ample storage is provided by a closet with sliding doors.

Guesthouse in Annapolis

Cozy Retreat w/Private Beach Access

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtful interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, couples romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

4.9 out of 5 average rating, 316 reviews

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Casa particular in Chestertown

A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.

4.93 out of 5 average rating, 168 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!

A charming white house with a steep roof and black shutters is displayed. The front porch features columns and seating areas, with potted plants lining the edges. An American flag hangs from the porch. Lush greenery surrounds the property, enhancing its inviting exterior.

4.97 out of 5 average rating, 112 reviews

The Patriot House-Chestertown, MD

Welcome to the Patriot House in Chestertown, Maryland. We recently renovated this beautiful home with a "Mad Men" Mid-Century modern vibe throughout. This is Two Units that combine together with connecting door for a total of 6 bedrooms and 3 remodeled bathrooms. You are renting entire first and second floors. Two kitchen and two living rooms. Wide front porch is perfect for cocktails or morning coffee. 2 blocks to Washington College and Downtown. We do not rent to undergrad students.

4.96 out of 5 average rating, 250 reviews

A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.

Apartment in Chestertown

Chestertown Private cottage with NFL Sun Ticket

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 the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

4.97 out of 5 average rating, 111 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.

4.98 out of 5 average rating, 651 reviews

A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.

Guest suite in Pasadena

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

4.97 out of 5 average rating, 282 reviews

A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.

Apartment in Essex

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Superhost

The master suite features wooden beams and log walls, creating a rustic atmosphere. A plush bed is positioned next to a classic bench. Soft lighting illuminates the space, while a colorful woven rug adds warmth to the wooden floor.

Cabin in Goldsboro

4.85 out of 5 average rating, 159 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

Popular amenities for Chestertown washer and dryer rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a washer and dryer

A charming corner of a historic building is showcased, featuring a prominent American flag flanked by potted greenery. The view extends down a quiet street, with a glimpse of an adjacent building in the background, enhancing the setting of Annapolis's historic district.

4.99 out of 5 average rating, 116 reviews

CIRCA 1885-Historic Annapolis-USNA GATE 1

A serene view of the Severn River is captured, bordered by lush greenery and blooming flowers. The calm water reflects the sky and surrounding landscape, while trees create a natural frame. Sunlight casts gentle shadows over the grassy area, enhancing the tranquil setting.

4.98 out of 5 average rating, 126 reviews

One bedroom apartment in Annapolis

4.89 out of 5 average rating, 85 reviews

The bedroom features a Queen-size bed with light bedding, complemented by a bedside table and lamp. A decorative chair and a small window allow natural light to fill the room, while a door provides access to the back porch.

Apartment in Chestertown

1-br apt in downtown Chestertown (Unit 1)

A king bed is dressed in a richly colored quilt featuring intricate patterns of gold and purple. Two decorative pillows add texture, while the exposed brick wall provides a historic backdrop. A bedside lamp casts a warm glow on the space.

4.88 out of 5 average rating, 100 reviews

Charming 18th C. Apt in DTA

4.97 out of 5 average rating, 276 reviews

A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.

Apartment in Chester

Cozy Waterfront Apartment Chester, MD

A cozy sleeping area is furnished with a wooden bed featuring a raised headboard. Soft beige bedding is complemented by a decorative pillow. Bedside tables with lamps provide warm lighting, creating an inviting space. A rug lies at the foot of the bed, enhancing the comfort.

4.96 out of 5 average rating, 162 reviews

Charming lower-level apartment in Annapolis

4.9 out of 5 average rating, 217 reviews

A serene view of the Chester River is presented, with soft pink clouds reflecting the sunset hues. Docked boats are visible along the wooden dock, while lush greenery frames the scene, providing a peaceful atmosphere at twilight.

Apartment in Grasonville

Halcyon house. Lovely views on MD eastern shore.

A colorful two-story building is presented, featuring bright blue siding and white trim around the windows. The entrance is marked by pink doors, and a red sign indicates a business within. Nearby streets and a gated area are visible, creating a lively atmosphere.

4.9 out of 5 average rating, 163 reviews

Eight Fleet - Annapolis Dock

House rentals with a washer and dryer

5 out of 5 average rating, 13 reviews

A cozy living area features a wooden table with chairs and a bowl of fruit. Blue and white patterned curtains frame the windows. An inviting seating area includes a striped chair and a small side table. A woven rug adds texture to the space.

Home in Betterton

Grandma’s Cottage

4.99 out of 5 average rating, 107 reviews

A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.

Home in Annapolis

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

4.96 out of 5 average rating, 97 reviews

River front cottage with private dock & water fun

Superhost

A wooden pier extends from the sandy shore towards a home surrounded by tall trees, with warm light glowing from large windows. The sky displays soft pink and blue hues as the day transitions to evening.

4.91 out of 5 average rating, 53 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

4.91 out of 5 average rating, 43 reviews

A spacious bedroom is illuminated by natural light from a window with light-colored blinds. A large bed with a dark headboard is centered in the room, accompanied by two pillows. Nearby, a floor lamp and a decorative curtain add soft accents to the neutral-toned walls.

Home in Rock Hall

The Blue Jimmy

A well-appointed bedroom features a spacious bed dressed in blue linens, complemented by decorative pillows. A cozy throw rests at the foot of the bed. A mounted artwork depicting a ship on the water is visible above the headboard, and soft lighting is provided by a bedside lamp.

5 out of 5 average rating, 86 reviews

Lovely Home in Chestertown With Free EV Charging

4.84 out of 5 average rating, 143 reviews

A charming two-story brick house is set in a grassy front yard, surrounded by neatly trimmed shrubs. The house features a steeply pitched roof and several windows that allow natural light. A driveway leads to the side of the property, providing access.

Home in Rock Hall

Pirates Perch

4.94 out of 5 average rating, 449 reviews

An open living area features hardwood flooring and large windows, allowing natural light to fill the space. A comfortable sectional sofa is positioned near a television. A kitchen island with seating complements the design, enhancing the inviting atmosphere of the home.

Home in Annapolis

New Hotel Chic

Condo rentals with a washer and dryer

A bright living room features large windows dressed with light curtains, allowing natural light to fill the space. A comfortable sofa and armchair are arranged around a sleek coffee table, with shelves displaying books and decorative items, contributing to a welcoming atmosphere.

4.98 out of 5 average rating, 156 reviews

New Downtown Annapolis Condo With Free Parking

A welcoming living area features two brown leather sofas adorned with blue patterned cushions. A wooden coffee table sits atop a blue geometric rug, and a small potted plant decorates the table. Natural light streams in from two windows beside the front door.

4.87 out of 5 average rating, 166 reviews

Capts Qrtrs - Awesome downtown Annapolis location!

5 out of 5 average rating, 29 reviews

A modern kitchen space is highlighted by stainless steel appliances and wooden accents. Two dining chairs are positioned around a wooden table beside a window, providing a view of the exterior. A patterned rug adds warmth to the wooden floor.

Condo in Chestertown

Historic Loft w/ Park View & Spa Access

A spacious living area is presented with a blue reclining sofa facing a large wall-mounted television. Warm wood cabinetry complements the kitchen area in the background, illuminated by soft lighting. A cozy electric fireplace adds warmth, creating an inviting space for relaxation.

4.84 out of 5 average rating, 83 reviews

Anchors Away

4.98 out of 5 average rating, 102 reviews

Charming Annapolis Waterfront Condo

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

4.97 out of 5 average rating, 68 reviews

Cozy Annapolis Condo

Superhost

A sandy beach stretches along the shoreline, dotted with parasols and beachgoers. Calm waters reflect a clear sky, while a pier juts out in the distance, framed by lush greenery. The serene landscape offers a tranquil view of the surrounding nature.

Condo in Betterton

4.9 out of 5 average rating, 42 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.