Chestertown

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$145

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Chester River House with Views

Chestertown house
3 BR / 1 BA / Sleeps 7 | Quick view
Excellent1 Reviews

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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

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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.

$95

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Charming Apartment in Historic Chestertown, MD

Chestertown condo
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent5 Reviews

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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.

    $120

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    Bayview by Chesapeake Bay

    Chestertown house
    1 BR / 1 BA / Sleeps 4 | Quick view
    Excellent2 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
    • Porch
    • 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!

    $280

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    Peaceful, Waterfront Home w/Pier on Kent Island

    Chester house – 19.2 mi away
    4 BR / 2 BA / Sleeps 8 | Quick view
    Excellent2 Reviews

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    Reviews

    (2)

    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The location is serene on a 3 …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Unbelievable value

    Left on Nov 04, 2010 for a stay in May 2010

    We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we…

    $350

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    Love Point Waterfront

    Kent Island house – 14.9 mi away
    3 BR / 2 BA / Sleeps 12 | Quick view
    Excellent4 Reviews

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    Reviews

    (4)

    Located on the Eastern shore of Maryland, Kent Island is a small area 13 miles long and 5 miles wide. The Bay Bridge spans the Cheasapeake bay from the Western shore to Kent Island. We are 4.5 miles north of the bridge in a charming old waterfront community called Love Point! Love Point is quiet area of single …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (4)

    Home away from Home , We feel the weight of the world disappear when we walk through the door.

    Left on Apr 17, 2015 for a stay in April 2015

    Paula's Bay House is home away from home. like visiting the vacation house your family has had for years. You have a wall of windows view of the water. We spend hours just watching the birds and the waves. At night we stoke up the fire and gaze at the flickering flames and just be in the moment of quiet and peaceful relaxation. This house is warm and eclectic , has all the modern conveniences…

    $250

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    * 3 Bedroom Rental House in Historic Rock Hall MD

    Rock Hall house – 8.2 mi away
    3 BR / 2 BA / Sleeps 7 | Quick view
    Excellent3 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!

    $295

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    Retreat at a quiet, water front cottage

    Chestertown house
    3 BR / 3 BA / Sleeps 8 | Quick view
    Excellent3 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.

    1 / 11

    $209

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    Love Point Bay Vacation Home

    Stevensville condo – 15.7 mi away
    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

    $250

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    Waterfront Cottage at Spring Cove

    Rock Hall cottage – 7.8 mi away
    3 BR / 2 BA / Sleeps 6 | Quick view
    Very Good2 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 …

    1 / 12

    $180

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    Captain's Quarters, a waterfront couples retreat

    Rock Hall condo – 7.9 mi away
    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
    1 / 15

    $262

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    Oak View Ridge

    Maryland house – 18.6 mi away
    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 …
    • Hot Tub/Jacuzzi
    • Fireplace
    • Parking
    • Grill
    • Television
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 / 5

    $115

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    Cozy Cottage close to a quiet beach.

    Galena cottage – 17.7 mi away
    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
    1 / 12

    $450

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    Chesapeake Bay Luxury Vacation Home, 5 Star

    Grasonville house – 15.7 mi away
    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
    1 / 8

    $250

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    Waterfront Boat Vacation Rental

    Davidsonville houseboat – 16.7 mi away
    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
    1 / 37

    $375

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    Luxury vacation condominum with private beach

    Chester house – 16.4 mi away
    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
    1 / 26

    $262

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    Sunrise Cove

    Maryland house – 18.6 mi away
    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
    • Hot Tub/Jacuzzi
    • Fireplace
    • A/C or climate control
    • Parking
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 / 28

    $647

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    Rest Assured

    Maryland house – 18.6 mi away
    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
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 / 13

    $487

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    Duck Cove at Wisp

    Maryland house – 18.6 mi away
    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
    1 / 10

    $190

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    In-town, pet-friendly Victorian cottage

    Chestertown cottage
    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Our Victorian cottage, built in the 1880s and upgraded to more modern standards, offers the best of both worlds: A bit of a rural feel, with a fenced-in side yard and back yard, a lovely porch swing, and ... easy strolling distance to the downtown historic Chestertown. Did you know that the fabulous Garden and Gun …
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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