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Chestertown Rental With Private Pool

Bedrooms 5
Property type house
Minimum Stay 2 - 6 nights


About the property

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, a large salt pool that is very private with depths ranging from 2 feet up to 8 feet, 1/2 of flat greenspace for lawn games, small pond, two charcoal grills, large outside seating area for dinner under the stars, comfortable lounge chairs. 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 kayak 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.

Please note that the house does not have WIFI and does not have television sets. We have used our hotspot on our phones for internet access and our laptops and tablets for tv access if needed,

More Details

Owner/Property Manager Stormy Lundy
Member since: 2015
Speaks English
Response time:
Within an hour
Response rate:
Calendar last updated:
24 July, 2017

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 & five miles from the center of Rock Hall with several marinas & the little beach.

A 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, three bathroom's perfect for a large group of friends & family.

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.


Accommodation and facilities for this holiday house in Chestertown in Pomona

Property Type:
  • house
  • Self-catering
House Rules:
  • Check-in: 13:00
  • /
  • Check-out: 12:00
  • Max. occupancy: 8 ...
  • Max. adults: 8
  • Min. age of primary renter: 25 ...
  • Children welcome ...
  • Parties/events not allowed ...
  • Pets not allowed ...
  • Non smoking only ...
  • When departing after your stay, the keys must be returned to the lockbox. All fans, lights, air units must be turned off, doors & windows must locked.
  • 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 ...
  • limited accessibility
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


Good! 3.8/5 -
(8 traveller reviews)

50% Complete
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Chestertown Rental With Private Pool
average rating of 3.75 based on 8 reviews
Crofton, MD

Great house, great value

  • 4 of 5

We have rented a house for the last seven summers and this house was by far the most clean, well stocked and prepared for a nice summer weekend. The pool is amazing. Overall, we had a great weekend and really enjoyed the house. The only reason we did not give it five stars is cause of the lack of wifi. I had no issues using my phone in the area, I just have limited data and did not always want to use my phone for that. Again, that's not a big deal to me, really nice area, if I am going to be in the area in the future, I will 100% use this house again.

  • Review Submitted: Jun 28, 2017
  • Date of Stay: Jun 2017
  • Source: HomeAway
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Comfortable, everything you need to relax!

  • 5 of 5

Our daughters wedding was in Chester town, the home of her fiancee'...we were able to all stay together as a family. It made our wedding weekend easy and relaxing. Everything we needed was right there and the pool kept the younger ones occupied in between wedding prep and the big event. Thank YOU!!

  • Review Submitted: Jun 12, 2017
  • Date of Stay: Jun 2017
  • Source: VRBO, from HomeAway
Owner's Response: Tracey it was a joy to host you and your family congratulations.
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Eh weekend away

  • 1 of 5

We arrived on a hot day to 0 air conditioning units in the house. After a phone call and a few text the units where installed. They where very noisey that my parents could not sleep so they ended up at a hotel for the other night. No TV even though the amenities said it did and even dvs players. It also showed a wifi symbol on the amenities yet did not have any in the hoyse. One of the last pictures was of what looked like a dock., which was perferect because I brought mine. Yet there was no dock at the property. Kids could not play outside because of ticks. The house was nice though. Plenty of room and it was clean. Owners where honest about the pool being open and gave ample warning of that. Do not know if we woyld go back because we rented under the facts of the site where not all correct. The location was close to the bay and Rock Hall which is a nice little town.

  • Review Submitted: May 22, 2017
  • Date of Stay: May 2017
  • Source: HomeAway
Owner's Response: Thank you for staying at the Sandybottom Retreat. We are very sorry this was not a fit for you & your family. Shortly after your call, we had someone install the units to each room within three hours. We have listed this home on VRBO for the past two seasons and have never stated that we provide WIFI or television access. Photo #21 is a photo of a local beach as we do mention that there are several small beaches located nearby, we have no mention of a dock, a beach or the house being located on the water in our complete description of the property nor is it mentioned in the caption of photo #21. This house is situated between nature conserve's in the back and across the road. Yes, I am certain there are ticks around, the ecologist's have warned the entire east coast of a heavy tick season this summer. Again, so sorry this was not a fit for you & your family and that your parents felt the need to stay in a hotel for Air Conditioning when the temperature on May 20th was 71 degrees during the day and 56 degrees that evening. Thank you, for staying at our rental.
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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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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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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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Nearest Airport
85 Miles
Nearest Barpub
5 Miles
Harbour Shack, Bay Wolf, Fish Whistle
Nearest Restaurant
7 Miles
Lemon Leaf, Chestertown Hotel,
Nearest Beach
3 Miles
Rock Hall, Tolchester, Betterton
Car: necessary


Prices & Availability

Prices for this holiday house in Chestertown, Maryland

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Nightly Rate
25 Aug 2017 - 25 Aug 2017
2 night minimum stay
for 2 nights
Nightly Rate
16 May 2018 - 16 May 2018
6 night minimum stay
for 6 nights
Nightly Rate
17 May 2018 - 20 May 2018
6 night minimum stay
for 6 nights
Nightly Rate
21 May 2018 - 21 May 2018
6 night minimum stay
for 6 nights
My Standard Rate
2 night minimum stay
for 2 nights

Additional pricing information

cleaning fee £76.94 + Tax
Property Damage Protection £60.78
Tax Rate 10.0%

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
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