Private pier and pool at this waterfront Chestertown home

Aerial view
5 bedrooms, desk, iron/ironing board, free WiFi
Fridge, microwave, oven, stovetop
Hair dryer, towels, soap, shampoo
5 bedrooms, desk, iron/ironing board, free WiFi

About this house rental

Situated in Chestertown, this lovely house for $711 per night is a fantastic choice for your next vacation. This private waterfront river home in beautiful historic Chestertown has its own private pier and pool - all on a quiet cul de sac. Enjoy the view from the river porch of the Eastern Shore sunset over glassy water, pick some Maryland Blue Crabs caught off the pier, and enjoy the light show at night with no winds to disturb the water surface. When summer is over, the home is a great place to stay during the hunting season. The landscape combined with the excellent game makes for one of the best hunting regions in the Northeast. The season begins in mid September and lasts through December. This house is less than 5 minutes from the quaint Main Street of Chestertown. The town dates back to the Revolution - in response to British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May 1774 and set forth “Resolves” forbidding importing, selling, or consuming of tea in Chestertown. The City re-enacts this event every year during the annual tossing Chestertown Tea Party Festival. If you consider yourself a foodie, you should spend your day touring one of the local farms or vineyards and then enjoy a meal at one of the many local restaurants. This home has a total of 5 Bedrooms and 4.5 Baths. There is Master en-suite bedroom on the Main Floor, 3 bedrooms and a combined Den/bedroom and full bath upstairs, and a recreation/bedroom space on the lower level complete with a pool table and a full bath. Both the main floor and upstairs each have oversized sun porches with views of the Bay. SLEEPING ARRANGEMENTS - all new beds on the 2nd floor! 5 Bedrooms/4.5 Baths; sleeps 12 adults (or 14 with children): Main Floor En Suite Master Bedroom: sleeps 2 -Queen Size Bed -En-Suite Full Bath Upstairs King Guest Room: sleeps 2 -King Bed -Shared Full Bath with 2 showers and double vanity in the Hall Upstairs Trundle Room: sleeps 2 -Twin Bed over Trundle Twin Bed -Shared Full Bath with 2 showers and double vanity in the Hall Upstairs Double Full Guest Room: sleeps 2-4 -Two Full Beds -Shared Full Bath with 2 showers and double vanity in the Hall Upstairs Den: sleeps 2 -Queen Pullout Sofabed -Shared Full Bath with 2 showers and double vanity in the Hall Lower Level Recreation Room: sleeps 2-4 -2 Queen Futon Beds -Full Bath HIGHLIGHTS: -Waterfront -Private backyard pool (Pool Closed October 31 through May 1) -Private Pier with boat slip, launching spot for kayaks (1 provided) or SUP boards (BYO). -Gas Grill - propane provided -Two sun porches with water views - one on the Main Floor and one upstairs -Dining Room table seats 6 -Breakfast Bar seats 2 -Breakfast table seats 2 -Poolside furniture -High Speed Internet and WiFi -3 TVs with fire stick -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for 3-4 cars on the circular driveway -Full Washer & dryer in Laundry Room -Dogs permitted with $250 pet fee paid prior to checkin. -Keyless entry. Drive straight to your rental home, enter the lock code on the front door to enter the home. Property Distance to: -Annapolis - 48 miles -Washington, DC - 75 miles -Baltimore - 75 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready made for you with freshly-laundered sheets & towels House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Pets permitted with $250 pet fee paid prior to checkin. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. Check-in time: 4:00 pm Check-out time: 11:00 am

Amenities

Pool
Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Parking
Laundry
Balcony / Patio
Dishwasher
TV
Garden

Map of Chestertown, MD

Reviews

4.8/5.0
Outstanding(22 Reviews)
5.0
Oct 2023
We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families .
5.0
Sep 2023
Great stay, comfortable for my family , overall had a great time!
5.0
Sep 2023
What a great spot for our family wedding weekend guests. So much room, well equipped and clean. Beautiful views and spectacular sunsets. Excellent communication with hosts as well. Thank you so much!
10.0
Aug 2023
It was an amazing vacation with children and grandchildren. Home was the perfect size for 11 people, pool so much funnnnnnnn, kids swimming in river at twilight, games in front yard, pool table, wonderful little town, great restaurants, 1/2 bushel of crabs one night (thanks, Clarks), Watershed Restaurant gift certificate, Tolchester Beach, nature preserve, Betterton. Nothing more peaceful than morning tea under trees by River and champagne on deck at sunset. And, oh, the Sunsets!!!!! Thank you for sharing your beautiful home for our week together.
5.0
Aug 2023
We thoroughly enjoyed our week at "Pier Pleasure." It was the perfect place to spend time with our children & grandchildren. The home was spacious & offered everyone private space... & also plenty of open areas to gather together to visit & "catch up." We enjoyed the comfort of the family room & the den...one for watching movies & the other for cozy visiting. Perhaps our greatest "pleasure" was the gorgeous pool (shaded in the afternoon!) & the open access to the water on the Chester River. Our son brought his fishing boat, & we enjoyed lots of fishing & boat rides. The young folks had a lot of fun kayaking also. We spent many hours of each day outdoors...in the pool & poolside. The hosts were very responsive to a minor maintenance issue that occurred & got things back on track. The downstairs Master Suite was really nice. In truth, it could actually use a new mattress...but it wouldn't stop us from reserving again! Mal & Anne
5.0
Jul 2023
It was an amazing vacation with children and grandchildren. Home was the perfect size for 11 people, pool so much funnnnnnnn, kids swimming in river at twilight, games in front yard, pool table, wonderful little town, great restaurants, 1/2 bushel of crabs one night (thanks, Clarks), Watershed Restaurant gift certificate, Tolchester Beach, nature preserve, Betterton. Nothing more peaceful than morning tea under trees by River and champagne on deck at sunset. And, oh, the Sunsets!!!!! Thank you for sharing your beautiful home for our week together.
5.0
Jul 2023
Great location with outstanding view of the Chester River. Home is well appointed and in wonderful condition. Beds were comfortable, there were plenty of good towels, and the complimentary toiletry travel packs are great touch. Kitchen is a bit small but has everything you need, including a fully stocked coffee/tea area with a Keurig pod/drip machine. We spent most of our time in the downstairs porch, which is air-conditioned and very welcome with the high temps we experienced. The only recommendations we have are for an umbrella for the outdoor table as there isn't much shade in the pool area, that the pool cleaner not run all day as it gets in the way, and maybe some more comfy chairs for the porch. We had a wonderful week and highly recommend Pier Pleasure!
10.0
Jul 2023
Very positive overall.

FAQs

How much does this house cost compared to others in Chestertown?

The average price for a rental in Chestertown is $199 per night. This rental is $512 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Private pier and pool at this waterfront Chestertown home. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Private pier and pool at this waterfront Chestertown home. Enjoy the water!

Is Private pier and pool at this waterfront Chestertown home pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Private pier and pool at this waterfront Chestertown home?

We found 11 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen / kitchenette, and internet / wifi.

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