Entire home

Private pier and pool at this waterfront Chestertown home

Photo gallery for Private pier and pool at this waterfront Chestertown home

Aerial view
Outdoor pool
Exterior
5 bedrooms, desk, iron/ironing board, free WiFi
Interior
Reviews
9.8

Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 14

Popular amenities

  • PoolPoolPool
  • WasherWasherWasher
  • KitchenKitchenKitchen
  • Air conditioningAir conditioningAir conditioning
  • Outdoor spaceOutdoor spaceOutdoor space
  • DryerDryerDryer

Explore 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

Most relevant reviews

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Languages

English

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 4 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Arcade/game room on site
  • Billiards/pool table on site
  • Kayak on site
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hunting nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • 1 unit
  • Garden

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

House Chestertown
8798
House Private vacation home
House Private vacation home Chestertown

About the area

Chestertown

Located in Chestertown, this vacation 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 Eastern Neck National Wildlife Refuge. Be sure to check out the area's animals with activities such as game walks and birdwatching.

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?

Check-out is at 11:00 AM.

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

Situated on the waterfront, this vacation 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 mi (25 km).

Reviews

9.8

Exceptional

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

Reviews

10/10 Excellent

Taraa W.

Liked: Cleanliness
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
Great stay
Great stay, comfortable for my family , overall had a great time!
Stayed 3 nights in Sep 2023

10/10 Excellent

Malcolm E.

Liked: Cleanliness
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
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

10/10 Excellent

Bill H., Pa

Liked: Cleanliness
Waterfront Gem
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!
Stayed 7 nights in Jul 2023

10/10 Excellent

Brewster F., Narberth

Liked: Cleanliness
Chestertown
Very positive overall.
Stayed 7 nights in Jun 2023

10/10 Excellent

Jen L.

Liked: Cleanliness
beautiful setting
This location was perfect and the views were lovely. Right on the Chester River with views of Chestertown. Very easy drive to the town. Great pier to sip coffee and enjoy the quiet of the river. House has so many amenities, just like someone's own home. Decor is a little outdated, but that wouldn't stop me from staying there again.
Stayed 3 nights in May 2023

8/10 Good

Sheri P., Fallsington PA

Liked: Cleanliness
Family gathering
We used this lovely waterfront home as part of a weekend celebration for out of town family and friends. Too early for the pool to be open, but the grounds were well kept and the river view is beautiful. The house was clean and well-appointed. The initial key code did not work, but we quickly got a new one. Only drawback was the sleeping arrangements: bedrooms were a little different than listed, and older mattresses and futons made sleeping somewhat uncomfortable. Overall a lovely weekend.
Stayed 3 nights in Apr 2023

10/10 Excellent

Rosario L.

Liked: Cleanliness
Beautiful home, excellent location
The property is beautiful and the location is perfect. The only upgrades I feel could be made would be some of the beds. The bed at the top of the stairs was so squeaky and noisy It would wake other people up. The room with the trundle bed would be better served with two single beds as the lower mattress that rolled out did not stay in the up position and had to stay on the floor. We wanted to utilize the futon in the basement, But it seems as if the heat did not work down there and it was too cold for anyone to sleep in. Other than that It was very nice and I would still come back.
Stayed 4 nights in Jan 2023

10/10 Excellent

Liza M.

Liked: Cleanliness
Family gathering for Thanksgiving
This home was perfect for our holiday gathering! Beautiful location on the river close to town with so many things to do for everyone in our family. The house was spacious and very clean, with great communication with our kind, accomodating hosts.
Stayed 4 nights in Nov 2022