Showing

PreviousNext property

$115

2 BR / 1 BA / Sleeps 5

Cozy Cottage close to a quiet beach. - Chestertown vacation rentals
1 / 5

$115

Book

Cozy Cottage close to a quiet beach.

2 BR / 1 BA / Sleeps 5 | Quick view

Details

A very relaxed area to go swimming, tubing, fishing and boating. You have to get in a car to go to a store about 2 miles for food , etc. We have nice restaurants near by and also golf about 5 miles down the road.
    • Suitable for children
    • Suitable for the elderly

    PreviousNext property

    $209

    2 BR / 1 BA / Sleeps 6

    Love Point Bay Vacation Home - Chestertown vacation rentals
    1 / 11

    $209

    Book

    Love Point Bay Vacation Home

    2 BR / 1 BA / Sleeps 6 | Quick view

    Details

    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave your worries behind …
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

      PreviousNext property

      $300

      4 BR / 2 BA / Sleeps 8

      3 Reviews

      $300

      Inquire

      Waterfront house Eastern Shore Chesapeake Bay

      4 BR / 2 BA / Sleeps 8 | Quick view
      “ Excellent ” 3 Reviews

      Details

      Reviews

      (3)

      This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake Bay. The property is …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Fireplace
      • Housekeeping Optional
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (3)

      Stress-free environment

      Left on Jan 30, 2013 for a stay in July 2011

      We have stayed at alan Fisher's Grove Creek home five times in the past six years and have enjoyed every stay. The home and grounds provide a stress-free environment that we look forward to each and every year. It is private and completely furnished with everything you need. All you require are your jeans and bathing suits. There is nothing like waking up in the morning and enjoying a few laps in…

      PreviousNext property

      $250

      3 BR / 2 BA / Sleeps 6

      2 Reviews

      $250

      Book

      Waterfront Cottage at Spring Cove

      3 BR / 2 BA / Sleeps 6 | Quick view
      “ Very Good ” 2 Reviews

      Details

      Reviews

      (2)

      The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented to outdoor living …
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (2)

      Laid back and relaxing

      Left on Aug 19, 2014 for a stay in August 2014

      My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no expectations besides having a place to relax and hang out. We were very pleased. For a price similar to what we may have paid for one motel room elsewhere, the cottage suited our needs very well, with a fully equipped …

      PreviousNext property

      $275

      2 BR / 3 BA / Sleeps 6

      3 Reviews

      $275

      Book

      WATERFRONT HOME+HOTTUB/WiFi/3DECKS/Pvt DOCK + MORE

      2 BR / 3 BA / Sleeps 6 | Quick view
      “ Excellent ” 3 Reviews

      Details

      Reviews

      (3)

      ************ RATE INCLUDES PLENTY OF ONSITE ACTIVITIES AND AMENITIES! ************** ****** THIS HOME IS A 2 BEDROOM PLUS A STUDIO APARTMENT UNIT IN LOWER LEVEL + 2.5 BATHS ****** PLEASE NOTE THAT RATES FOR PERIODS OF SPECIAL EVENTS LIKE THE STADIUM GAMES, ETC. ARE NOT NOTED HERE. CONTACT OWNER FOR THOSE RATES…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Housekeeping Optional
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (3)

      Wonderfully Serene and Fun Getaway!

      Left on Mar 29, 2014 for a stay in March 2014

      I stayed here in the recent past and decided to stay here again recently. Even though this visit was not as long, it was just as wonderful. We loved our first stay and this is why we came back and will continue to rent with Dale and Joy in the future as they were very accommodating and genuine from the beginning of our search process through the end of our stay, each time. Also very efficient …

      PreviousNext property

      $450

      4 BR / 3 BA / Sleeps 10

      Chesapeake Bay Luxury Vacation Home, 5 Star - Chestertown vacation rentals
      1 / 12

      $450

      Inquire

      Chesapeake Bay Luxury Vacation Home, 5 Star

      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other accommodations do not. For large…
      • Waterfront
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Washing Machine
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $262

      4 BR / 4 BA / Sleeps 11

      1 / 11

      $262

      Inquire

      Sunrise Cove

      4 BR / 4 BA / Sleeps 11 | Quick view

      Details

      Bedding: King, Queen, Bunk w/trundle, Double, QSS, TSS Create unforgettable moments with family and friends when you stay in the delightful 4 bedroom lake access home Sunrise Cove. This stunning home, with its stylish décor and open floor plan, boasts the ultimate in comfort and relaxation. Fall in the love with the …
      • Ocean or water views
      • Fireplace
      • A/C or climate control
      • Parking
      • Grill
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $247

      3 BR / 3 BA / Sleeps 8

      1 / 15

      $247

      Inquire

      Oak View Ridge

      3 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Bedding: Queen, Queen, 2 Twins, Double Air Mattress Delightful enchantment is what you will experience the moment that you step inside the log home Oak View Ridge. The Great Room speaks of warmth and comfort with gorgeous hardwood floors and expansive vaulted ceilings. Cuddle up in front of a crackling fireplace or …
      • Fireplace
      • Parking
      • Grill
      • Television
      • DVD Player
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $487

      6 BR / 3 BA / Sleeps 16

      1 / 4

      $487

      Inquire

      Duck Cove at Wisp

      6 BR / 3 BA / Sleeps 16 | Quick view

      Details

      Community: Lake Pointe Bedding: King, Queen, Queen, Queen, Queen, 2 Twins, 2 Queen Sleeper Sofas Dove Cove at Wisp offers prime location, the most desirable amenities and the promise for an extraordinary Deep Creek vacation! Located in the prestigious community of Lake Pointe at Wisp, this home will put you in the …
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Fireplace
      • A/C or climate control
      • Grill
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $647

      5 BR / 5 BA / Sleeps 14

      1 / 24

      $647

      Inquire

      Rest Assured

      5 BR / 5 BA / Sleeps 14 | Quick view

      Details

      Bedding: King, Queen, Queen, 2 Bunkbeds, 2 Bunkbeds Be “Rest Assured” that you will have a truly magical Deep Creek experience when you choose to stay in this fabulous 5 bedroom lakefront home. Evidently furnished and designed with a great deal of love and pride, you will quickly fall in love with all of the …
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Fireplace
      • A/C or climate control
      • Television
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      PreviousNext property

      $110

      1 BR / 1 BA / Sleeps 4

      2 Reviews

      $110

      Book

      Bayview by Chesapeake Bay

      1 BR / 1 BA / Sleeps 4 | Quick view
      “ Excellent ” 2 Reviews

      Details

      Reviews

      (2)

      This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen, living room, bedroom…
      • Ocean or water views
      • Internet Access
      • Outdoor Dining Area
      • A/C or climate control
      • Patio
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (2)

      Bayview cottage

      Left on Jun 09, 2014 for a stay in June 2014

      I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and a well appointed kitchen. After sleeping soundly, we awoke to the sight and sounds of songbirds in the yard and eagles, herons, and osprey flying over the Bay. Francesca is the perfect hostess!

      PreviousNext property

      $180

      1 BR / 1 BA / Sleeps 4

      1 / 12

      $180

      Book

      Captain's Quarters, a waterfront couples retreat

      1 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and casual meals …
      • Pet friendly - ask
      • Suitable for children - ask

      PreviousNext property

      $295

      3 BR / 3 BA / Sleeps 8

      3 Reviews

      $295

      Book

      Retreat at a quiet, water front cottage

      3 BR / 3 BA / Sleeps 8 | Quick view
      “ Excellent ” 3 Reviews

      Details

      Reviews

      (3)

      Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent County area. This south …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Fireplace
      • Washing Machine
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (3)

      Construction in progress and mud everywhere.

      Left on Oct 18, 2014 for a stay in October 2014

      If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.

      PreviousNext property

      $145

      3 BR / 1 BA / Sleeps 7

      1 Reviews

      $145

      Book

      Chester River House with Views

      3 BR / 1 BA / Sleeps 7 | Quick view
      “ Excellent ” 1 Reviews

      Details

      Reviews

      (1)

      A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in…
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (1)

      A PLEASANT STAY

      Left on Aug 29, 2014 for a stay in August 2014

      what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.

      PreviousNext property

      $375

      4 BR / 4 BA / Sleeps 10

      1 / 37

      $375

      Inquire

      Luxury vacation condominum with private beach

      4 BR / 4 BA / Sleeps 10 | Quick view

      Details

      Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen size bed for the 4…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Fireplace
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $95

      1 BR / 1 BA / Sleeps 4

      5 Reviews

      $95

      Book

      Charming Apartment in Historic Chestertown, MD

      1 BR / 1 BA / Sleeps 4 | Quick view
      “ Excellent ” 5 Reviews

      Details

      Reviews

      (5)

      This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe table and chairs is a …
      • Waterfront
      • Internet Access
      • Outdoor Dining Area
      • A/C or climate control
      • Central heating

      Details

      Reviews

      (5)

      Cute little apartment right in Chestertiwn.

      Left on Jun 05, 2014 for a stay in May 2014

      The apartment in Chestertown is super cute and convenient. Walking distance to the water and all the cute cafés and restaurants. Clean and simple with a cute little balcony. The place was great and the hosts were helpful and responsive.

      PreviousNext property

      $250

      2 BR / 2 BA / Sleeps 4

      1 / 8

      $250

      Book

      Waterfront Boat Vacation Rental

      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      2 bedroom, 2 bath with living salon, kitchen, and an aft deck
      • Waterfront
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $250

      3 BR / 2 BA / Sleeps 7

      3 Reviews

      $250

      Book

      * 3 Bedroom Rental House in Historic Rock Hall MD

      3 BR / 2 BA / Sleeps 7 | Quick view
      “ Excellent ” 3 Reviews

      Details

      Reviews

      (3)

      This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s Crab House, The …
      • Shared outdoor pool (unheated)
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (3)

      Excellent Value in a Great Location

      Left on Apr 18, 2012 for a stay in May 2011

      We have rented this home on several occasions over the past few years, and always found everything clean and in good working order. The large back yard is great for activities with our grandkids. Easy walking distance to Watermen's Restaurant and The Harbour Shack is a real bonus. Highly recommended!

      PreviousNext property

      $259

      1 BR / 1 BA / Sleeps 2

      1 / 9

      $259

      Book

      Camellia Cottage, Chestertown, MD

      1 BR / 1 BA / Sleeps 2 | Quick view

      Details

      Camellia Cottage is a ca. 1950 ranch house apartment located on the property of the award-winning Brampton Bed & Breakfast Inn. The newest accommodation at our Chestertown Bed and Breakfast is a chic, Danish Modern furnished one bedroom flat. With it's own entrance, a fully equipped kitchen and a large living and …
      • Internet Access
      • Housekeeping Optional
      • A/C or climate control
      • Central heating
      • Parking
      • Pet friendly
      • Suitable for the elderly
      • Wheelchair accessible - ask

      Looking for more rentals?


      We're showing only results that match your dates and preferences.


      See all 19 Chestertown rentals, all 46 Chesapeake Bay rentals, or start a new search.


      There are no more results in Chestertown. Top of page