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Private pier and pool at this waterfront Chestertown home

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Welcome to Pier Pleasure!
The waterfront pool is ready and awaiting your summer vacation!
The home is both waterfront and has its own private pool.
The Main Floor Master Suite has water views.
Enjoy fishing, kayaking or boating from the private pier (boat slips are available upon requests).
Reviews
9.8 out of 10 Exceptional
5 bedrooms3+ bathroomsSleeps 14

Popular amenities

  • PoolPoolPool
  • Pet-friendlyPet-friendlyPet-friendly
  • Free WiFiFree WiFiFree WiFi
  • KitchenKitchenKitchen
  • WasherWasherWasher
  • DryerDryerDryer

Check out the area

Map
Chestertown, MD
  • Popular LocationRiver Arts Chestertown3 min drive
  • Popular LocationWashington College3 min drive
  • Popular LocationRolphs Wharf Marina10 min drive
  • AirportAberdeen, MD (APG-Phillips Army Airfield)92 min drive

Rooms & beds

5 bedrooms (sleeps 14)

Lower Level Rec Room

2 Double Sofa Beds

Main Level Queen Suite

1 Queen Bed

Upstairs Den

1 Double Sofa Bed

Upstairs Double Full Guest Room

2 Double Beds

Upstairs King Guest Room

1 King Bed

Upstairs Trundle Room

2 Single Beds

3 bathrooms, 1 half bathroom

Lower Level Basement

Toilet · Shower only

Main Floor Master

Bathtub or shower · Toilet

Main Floor Powder Room

Toilet

Upstairs Shared Hall

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

Private pier and pool at this waterfront Chestertown home

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

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host
Premier Host

Languages

English

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. Rolphs Wharf Marina and Rock Hall Harbor are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Betterton Beach and Love Point State Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 3 min drive
  • River Arts Chestertown - 3 min drive
  • Wilmer Park - 3 min drive
  • Washington College - 3 min drive
  • Rolphs Wharf Marina - 10 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • McDonald's - 5 min drive
  • Procolino Pizza - 5 min drive
  • Dining Hall - 4 min drive
  • Luisas Cafe - 5 min drive
  • Uncle Charlie's Bistro - 4 min drive

Frequently asked questions

Does Private pier and pool at this waterfront Chestertown home have a pool?

Yes, this property has an outdoor pool.

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

Yes, pets are allowed at this property.

What time is check-in at Private pier and pool at this waterfront Chestertown home?

Check-in begins at 4:00 PM.

What time is check-out at Private pier and pool at this waterfront Chestertown home?

Checkout is at 11:00 AM.

Where is Private pier and pool at this waterfront Chestertown home located?

Situated on the waterfront, this holiday home is 1.6 mi (2.5 km) from Washington College and 4.2 mi (6.7 km) from Rolphs Wharf Marina. Betterton Beach and Rock Hall Harbor are also within 16 miles (25 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 19 out of 22 reviews" "
Rating 8 - Good. 3 out of 22 reviews" "
Rating 6 - Okay. 0 out of 22 reviews" "
Rating 4 - Poor. 0 out of 22 reviews" "
Rating 2 - Terrible. 0 out of 22 reviews" "

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Taraa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wood family loved Pier pleasure
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 .
Stayed 3 nights in Oct 2023

10/10 Excellent

Jonathan b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Great stay, comfortable for my family , overall had a great time!
Stayed 3 nights in Sep 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Awesome location!
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!

10/10 Excellent

Malcolm E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for our family vacation!
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
Stayed 6 nights in Jul 2023

10/10 Excellent

Mary S., Abington

Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary
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.
Stayed 7 nights in Jul 2023

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

Premier Host
They consistently provide great experiences for their guests
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