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Chestertown Rental With Private Pool

5 Reviews
Bedrooms 5
Property type house
Minimum Stay 2 nights

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Minimum Stay
2 nights


Photos and Description of this 5 bedroom holiday home in Chestertown - Sandy Bottom Retreat

4 Bedrooms, 3 Bathrooms, Sleeps 8

Located a short drive from the center of historic Chestertown the county seat of Kent County, Maryland. This vacation rental has a lot to offer, large salt pool that is very private with depths ranging from 2 feet up to 8 feet, 1/2 of flat green space for lawn games, small pond, two charcoal grills, large outside seating area for dinner under the stars, comfortable lounge chairs and lots of pool floats. This is the perfect getaway with a fully stocked Kitchen for those who like to cook. Four very comfortable bedrooms and Three bathrooms.

The center of Chestertown offers something for everyone, with great little restaurants a vibrant fresh & local Farmer's Market on Saturday's, great little shops, a bookstore, coffee shop and a first run movie theater. Great bike trails, nearby boating or kayaking rentals and a handful of small beaches to visit. For those of you who love history . . . Chestertown has a very rich history starting with the founding of Washington College in 1782 one of the oldest Liberal Arts Colleges in the country.

  • Minimum Age Limit for Renters
  • children welcome
  • limited accessibility
  • non smoking only
  • pets not allowed

Owner/Property Manager Stormy Lundy
Member since: 2015
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
8 October, 2016

About Owner/Property Manager Stormy Lundy

World Traveller, Dog lover, sorry we are all allergic to cats in this house. Nature lover and certainly in love with Chestertown Maryland. I have been a big fan for the last twenty five years and finally took the plunge with a group of very good friends to purchase a nice relaxing getaway in Chestertown.

Owner/Property Manager Stormy Lundy purchased this house in 2002

Why Owner/Property Manager Stormy Lundy chose Chesapeake Bay

Beautiful plot of land surrounded by nature but only 7 miles from the center of Chestertown.

Lovely rancher in excellent shape with enough bedrooms and space to accommodate a large group yet, comfortable enough just to get away alone from time to time. the house contains two master suite's and three bathroom's which make it perfect for all of us.

What makes this house unique

The house is large enough that you never feel on top of each other.

We had the pool converted from chlorine to salt a few years ago it is much nicer and cleaner and certainly better for your skin & hair.

The house faces and backs up to a nature preserve so no one can build behind us or in front of us.

It is very peaceful and the air is fresh & clean, we are always delighted to see turtles, fox, turkey's & eagle's outside.

We have a half acre pond in the back stocked with fish, great for a relaxing catch & release.

We also have a good friend who keeps several Bee Hives on the property, nothing like your own local honey.


based on 5 holidaymaker reviews

Chestertown Rental With Private Pool
average rating of 4.0 based on 5 reviews

Grandchildren loved the pool

  • 5 of 5

Our family included grandparents, two daughters, and four grandchildren aged 3 to 7. We really enjoyed the beautiful clean large pool. The house gave us plenty of room. All beds were comfortable. Three bathrooms were a plus. The house is very comfortable. The kitchen well equipped. Our grandchildren all want to come back.

Thank you for sharing your vacation home.

  • Review Submitted: Aug 27, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Mary, We are thrilled you and your family had a five star stay ! The house was left in great shape. We look forward to hosting you next season.
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0 0
baltimore, md

Amazing pool! Quiet area

  • 4 of 5

The house was clean and nice. The area very laid back and quiet. The crown piece is the huge beautiful pool. Owner was very responsive and helpful. Great for our family vacation

  • Review Submitted: Aug 22, 2016
  • Date of Stay: Aug 2016
  • Source: HomeAway
Owner's Response: Thank you, we are thrilled that you enjoyed your stay and the use of the amazing salt pool it is more than relaxing on a hot summer's day. Thanks for staying, so happy you enjoyed the lovely little town as well.
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0 0
Chestertown, MD

Lovely place at a reasonable price. And a glorious pool!

  • 5 of 5

My family stayed here this past weekend for my wedding and loved it. Accommodations were excellent, the house immaculate, plenty of bedrooms and baths. And the pool was the best! Only seven minutes to Chestertown. Owner is easy to work with. I would book this again in a heartbeat, but, frankly, I do not want to get married again!

  • Review Submitted: Jun 29, 2016
  • Date of Stay: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thom, we were thrilled to host your family for the wedding and we were also very pleased to know all of your guests had a great time. The house was left in great shape thank you so much!
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0 0

Wonderful stay in a little slice of french country in Chestertown

  • 5 of 5

This house is warm, gracious and welcoming when you arrive. Everything you need within 15 minutes of downtown Chestertown or Rock Hall. The pool was fun, we had a lovely barbecue, and were able to enjoy friends and family the night before our wedding in a relaxed and homey space. The owners are responsive and helpful and everything you need is right there. There is no internet so bring your own hotspot but otherwise, wonderful stay.

  • Review Submitted: Sep 15, 2015
  • Date of Stay: Sep 2015
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Amy, As per norm happy to hear you and your family and guest's enjoyed your stay at our getaway. So nice to hear it was just as you imagined for the night before your Wedding. So happy it all worked for your families big brunch the next day as well. The house was left in great shape & tidy with everything placed in the recycle bins and laundry room. thank you for taking such good care. congratulations !
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1 1


  • 1 of 5

This property was dirty and smelled like a moldy basement.One bedroom could not be slept in as it smelled strongly of cat urine.Some of the bed linens were stained and the outside furniture was dilapidated and rusty.The place was so bad that we cut our stay short and went home a day early.

  • Review Submitted: Sep 8, 2015
  • Date of Stay: Aug 2015
  • Source: VRBO, from HomeAway
Owner's Response: It has been my policy and will continue to be my policy to call or text each guest to make certain everything is in order and as expected on the first day of their stay. Our home is cleaned by a local professional the day before the arrival of guests, it has been the case for each and every rental this Summer. I personally assisted in the late August cleaning to make certain things were in proper order because the property has been very popular and rented the entire month of August. This property has no basement, the cleaning professional who attends to the property reported no smell when cleaning on the 1st of September. The owners of the property were in residence the evening of September 2nd for the long weekend there was no odor or smell of anything other than the thriving honeysuckle bush outside the bedroom in question. There are no cats on the property and there never will be, three of the owners happen to be allergic to cats one of the owners has asthma. I replaced the one outside chair that was broken on the patio this past weekend and Purchased four new Sunbrella Chaise Loungers. We continue to be very proud, very clean, & responsible owners.
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2 2


Nearest Airport
85 Miles
Nearest Barpub
5 Miles
Harbour Shack, Bay Wolf, Fish Whistle
Nearest Beach
3 Miles
Rock Hall, Tolchester, Betterton
Car: necessary


Prices & Availability

Prices for this holiday house in Chestertown, Chesapeake Bay

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Fall Winter
3 Oct 2016 - 20 Mar 2017
2 night minimum stay
for 2 nights
My Standard Rate
2 night minimum stay
for 2 nights

Additional pricing information

Property Damage Protection £65
cleaning fee £82 + Tax
Tax Rate 10.0%

Owner's Cancellation Policy

  • 100% refund for cancellations more than 60 days before check-in date.
Enter dates for accurate pricing
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Available arrival


Accommodation and facilities for this holiday house in Chestertown in Maryland

Property Type:
  • house
  • Self-catering
  • Away From It All
  • Family
  • Historic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Hob ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • Bathroom 1 - Toilet , Shower Enclosure
    Bathroom 2 - Toilet , Shower Enclosure
    Bathroom 3 - Toilet , Bath with Shower
  • 5 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 Double Bed , This bedroom also has an ensuite bathroom
    Bedroom 2 - 1 Double Bed , This bedroom also has an ensuite bathroom
    Bedroom 4 - 1 Large Double Bed , This bedroom has a large shared bathroom with tub & Shower
    Bedroom 3 - 1 Double Bed , This bedroom has a shared bathroom with a Tub & Shower
    Bedroom 5 - 1 Single Bed , Shared Bathroom
  • Books
  • DVD Player ...
  • Games ...
  • Stereo ...
  • Television ...
  • Terrace ...
  • Kayak / Canoe ...
  • Garden
  • Barbecue ...
  • Tennis ...
  • Minimum Age Limit for Renters
  • children welcome
  • limited accessibility
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Private Pool ...
  • churches
  • cinemas
  • festivals
  • Health/Beauty Spa
  • library
  • live theatre
  • marina
  • playground
  • recreation centre
  • restaurants
  • winery tours
Leisure Activities:
  • antique hunting
  • beachcombing
  • bird watching
  • Boating
  • horse riding
  • Horseshoes
  • Miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hunting
  • jet skiing
  • Kayaking
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • bay fishing
  • swimming
  • tennis
  • water tubing
  • wind-surfing

Partner Offers

Portable wifi hotspot

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