Vacation rentals in Chestertown, MD

This apartment is conveniently located just around the corner from Great Oak Manor Wedding Venue, within walking distance of Great Oak Landing Marina and Jellyfish Joel's Beach Bar. It has excellent user, location, and cleanliness ratings.
The apartment has 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a gourmet kitchen, a lazy front porch with wildlife sightings, air conditioning, a garden, parking, and internet. Guests can enjoy a 9-hole golf course on the marina property, boat and jet ski rentals, local fishing boat charters on the Chesapeake Bay, and proximity to historic Chestertown, Washington College, and quaint shops and pubs in Rock Hall.

This waterfront vacation home in Rock Hall is close to The Mainstay, Rock Hall Harbor, and Waterman's Museum, all within a 3-mile radius. It has excellent user, location, and cleanliness ratings.
The house has one bedroom and can accommodate up to 7 guests. It features a fully equipped kitchen, two bathrooms, a garden, and a smoke-free environment. Guests can enjoy amenities such as air conditioning, a terrace or balcony, parking, a washing machine, a TV, and a coffee/tea maker.

Apartment listing for up to 4 guests with an excellent rating of 100% based on 86 reviews. Your accommodation will be located in Chestertown.
Services and facilities include a garden, a kitchen and air conditioning.

Vacation house rental with an excellent rating of 100% based on 54 reviews. You will stay in Rock Hall.
Facilities and services: a garden, a kitchen and free parking.

Accommodation with an excellent rating of 100% based on 146 reviews. This accommodation is based in Rock Hall.
Facilities and services: free parking, air conditioning and a kitchen. Pets are allowed in this house.

Bay Haven Cottage is an excellent-rated cottage located in a historic fishing village on the Chesapeake Bay. It's within walking distance to restaurants, cafes, bars, shops, and the beach.
With a floor area of 1190 square feet, this 2-bedroom, 2-bathroom cottage can accommodate up to 4 guests. It offers modern amenities such as WiFi, Netflix, Hulu, Alexa, flat-screen TVs, and gel foam mattresses. Guests can also enjoy a fully stocked kitchen, a garden, a spa, and parking.

Accommodation at 1101 dollars for 14 people with an excellent rating of 98% based on 19 reviews. This accommodation is based in Chestertown.
Facilities and services include a pool table, a garden and a dish washer. Take advantage of the air conditioning in this apartment in Chestertown.

Book this vacation rental with an excellent rating of 96% based on 46 reviews. Your accommodation will be located in Rock Hall.
Services and facilities include free parking, a kitchen and a washing machine. Take advantage of the garden in this house!

Vacation rental with an excellent rating of 100% based on 74 reviews. This accommodation is located in Rock Hall.
Facilities and services include a dish washer, air conditioning and free parking.

House for up to 6 guests with an excellent rating of 97% based on 158 reviews. You will stay in Kingstown.
Facilities and services: free parking, a garden and a coffee place. Pets are allowed in this house.

House listing for 8 people with an excellent rating of 99% based on 73 reviews. You will be in Rock Hall.
Facilities and services include a garden, a fridge and a barbecue. Enjoy free parking with this accommodation in Rock Hall!

This cottage is set amidst meadows and woodland, offering a serene escape with abundant birdwatching opportunities. It is situated within the grounds of an 18th-century farm on the eastern shore of Chesapeake Bay, in Edesville. The cottage has excellent user, location, and cleanliness ratings.
It has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. The open-concept kitchen, dining, and living area feature high ceilings and a teak dining table for six. Amenities include a gas fireplace, central heat and AC, 5G fiber, smart TVs, a Keurig coffee maker, a washer and dryer, and basic toiletries. Guests have access to a shared pool (with designated hours) and a dock for watercraft enthusiasts.

Book this vacation rental from 285 dollars for 4 people. You will be based in Rock Hall.
Facilities and services include a dish washer, a fridge and a washing machine. Take advantage of the garden in this apartment!

Book this vacation rental with an excellent rating of 94% based on 12 reviews. Your accommodation will be located in Rock Hall.
Services and facilities: a dish washer, a kitchen and air conditioning. Take advantage of the garden in this house in Rock Hall.

House listing for up to 9 guests with an excellent rating of 99% based on 55 reviews. You will be based in Tolchester.
Services and facilities: a tennis court, a barbecue and a freeze. This house also has a terrace!

Book this vacation rental for 4 guests with an excellent rating of 99% based on 38 reviews. This accommodation is based in Chestertown.
Services and facilities include a freeze, air conditioning and a washing machine. This apartment also has a garden!

Book this vacation rental from $258 per night for 9 guests with an excellent rating of 100% based on 7 reviews. You will be in Rock Hall.
Facilities and services include a garden, a washing machine and a dish washer. This apartment in Rock Hall is ideal for families.

This apartment is located in the city center of Rock Hall, within walking distance to shops, restaurants, and the waterfront. It has excellent user ratings. The apartment has 3 bedrooms, 1 bathroom, and a floor area of 1310 square feet, and can accommodate up to 5 guests.
The apartment features a charming coastal and nautical decor, air conditioning, a terrace or balcony, a garden, parking, a kitchen with a fridge, microwave oven, and dishwasher, and modern amenities. It is pet-friendly and family-friendly. Nearby attractions include Sandy Beach at Ferry Park, The Mainstay, Rock Hall Liquors, Blue Crab Chesapeake Charters, and East Neck Island.

Oyster Cottage is a pet-friendly cottage in Rock Hall, MD, just steps away from shopping, dining, and the waterfront. It has an excellent user rating and can accommodate up to 7 guests.
The cottage has two living room spaces, a well-equipped kitchen, an outdoor living space with a grill, and a unique side garden. It also has air conditioning, a Jacuzzi, a terrace/balcony, a garden, parking, and internet access.

Apartment for up to 8 people with an excellent rating of 100% based on 2 reviews. This accommodation is based in Chestertown.
Services and facilities include an iron, a kitchen and free parking. This apartment in Chestertown is ideal for families.

Apartment rental from $420 for 8 people. You will stay in Chestertown.
Services and facilities include a fridge, a washing machine and a terrace.

Apartment listing for 15 people with an excellent rating of 100% based on 51 reviews. This accommodation is located in Chestertown.
Facilities and services include a dish washer, an iron and a spa. Take advantage of the air conditioning in this apartment in Chestertown.

Vacation house to rent for up to 7 guests with an excellent rating of 98% based on 30 reviews. You will be in Rock Hall.
Facilities and services: free parking, a barbecue and a kitchen. This house in Rock Hall also has a garden!

House for 6 guests with an excellent rating of 98% based on 27 reviews. You will be based in Rock Hall.
Services and facilities include a coffee place, a dish washer and a garden. This house in Rock Hall also has air conditioning!

Vacation rental listing for 6 guests with an excellent rating of 94% based on 2 reviews. You will stay in Rock Hall.
Facilities and services include a dish washer, a garden and a terrace. Take advantage of the air conditioning in this apartment in Rock Hall.