Pier Pleasure

5 BR
4.5 Baths
Sleeps 14


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



-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

205 Fey Rd Chestertown, MD 21620

Sleeping Arrangements

Main Level Queen Suite Queen
Upstairs King Guest Room King
Upstairs Trundle Room Twin (2)
Upstairs Double Full Guest Room Full (2)
Upstairs Den Sofa Queen
Lower Level Rec Room Sofa Queen (2)

Bathroom Configuration

Main Floor Master: Toilet, Combo Tub Shower
Upstairs Shared Hall: Shower, Toilet, Combo Tub Shower
Lower Level Basement: Shower, Toilet
Main Floor Powder Room: Toilet

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
BBQ Grill
Bath Towels
Bay View
Beach chairs
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Covered Patio
Dedicated work space
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Parking Available
Pets Considered
Pool table
Private Backyard
Private Backyard Pool
Private Fishing Pier
Private Pier
Private Pool
Private entrance
Self Check-In
Smoke Detector
Smoke alarms
Travel crib
Washing Machine
Water View
body wash
hot water
portable crib



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit Pier Pleasure. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.


Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. 


Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.


No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.


If you wish to bring your dog, you will need to pay the $250 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner.


Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.


There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.


No compensation will be given for temporary outage of electricity, gas, water or cable. 


Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.


Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).


  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 14 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
  8. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.


Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 14 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.


iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.


Loving pier pleasure
5/5 stars
We loved staying at pier pleasure . The beds were comfortable. A great home for 2 families . The view of the chester river was fantastic. We enjoyed sitting on the pier and looking at the water and boats passing by.
- Taraa
Great Stay!
5/5 stars
Had a great stay! For a family of 10 was very spacious and comfortable, as well as clean! Plus shopping was a mile away. Thank you for your hospitality iTrip! J.Bailey
- Jonathan
Awesome location!
5/5 stars
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!
- Jane
iTrip Review
5/5 stars
Had a great stay. Kids loved the pool and fishing from the dock. Beautiful sunsets on the water. Definitely would stay again.
- Dwight

Book Your Stay

Select your trip dates.
Contact Manager

Phone (410) 571-4076