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Private pier and pool at this waterfront Chestertown home

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

Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 14

Popular amenities

  • Washer
    WasherWasher
  • Pool
    PoolPool
  • Pet-friendly
    Pet-friendlyPet-friendly
  • Outdoor space
    Outdoor spaceOutdoor space
  • Kitchen
    KitchenKitchen
  • Air conditioning
    Air conditioningAir conditioning

Check-in time

4:00 PM

Check-out time

11:00 AM

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

Room options

About the area

Chestertown

At this holiday home, you'll be 2.4 km (1.5 mi) from Washington College and 6.7 km (4.2 mi) from Rolphs Wharf Marina. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 3.5 bathrooms and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A sofa bed, a living room and a Smart TV are also available. .This pet-friendly holiday home offers an outdoor pool, a games room and a garden. .Attractions in proximity to this Chestertown holiday home include Sandy Point State Park and Chesapeake Bay Bridge.

What's nearby

  • Historical Society of Kent County Maryland - 3 min drive
  • Garfield Center for the Arts at the Prince Theater - 3 min drive
  • River Arts Chestertown - 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

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 transport

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 3.5 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 centre
  • 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

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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 are welcome
  • Service animals 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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation. Contactless check-in is available.

Property is also known as

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

Frequently asked questions

Are there any beaches close to Private pier and pool at this waterfront Chestertown home?

The closest beach to Private pier and pool at this waterfront Chestertown home is Sandy Point Beach (36.9 km).

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

Private pier and pool at this waterfront Chestertown home has a pool.

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

This property features an outdoor pool, as well as a private pool and a living room.

Is there a private hot tub at Private pier and pool at this waterfront Chestertown home?

No, but there is a private pool.

Is there a free airport shuttle available at Private pier and pool at this waterfront Chestertown home?

No, Private pier and pool at this waterfront Chestertown home does not offer an airport shuttle service.

What time are check-in & check-out at Private pier and pool at this waterfront Chestertown home?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Private pier and pool at this waterfront Chestertown home Reviews

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

8/10 Good

Laura R.

Liked: Cleanliness
Great property and so much to do!
We stayed for a long weekend for a family anniversary and had a lovely time. The property is gorgeous and well maintained. The dock (perfect for crabbing); the pool (clean and refreshing), the two porches on both floors (gorgeous views) and a well stocked house with everything you need. Plenty of space and rooms for all. We really had a lovely weekend.
Stayed 3 nights in Sep 2022

10/10 Excellent

Paola R.

Liked: Cleanliness
Loved the place.
Our only observation were the beds. We found them to be outdated and uncomfortable.
Stayed 3 nights in Aug 2022

10/10 Excellent

Shannon I.

Liked: Cleanliness
Amazing place
This house was amazing! It had more than enough room for our group of 8. We even managed several games of hide and seek. The pool was excellent and we had the most beautiful view of the river. Our only hiccups were some issue with the upstairs cooling (though we were able to use the 2 available window units to survive) and we could only find the remotes to 1 tv. I would suggest a TV in the basement for the "hangout" spot but it was not a detrement to our stay at all.
Stayed 6 nights in Jul 2022

10/10 Excellent

Kim L.

Liked: Cleanliness
Gorgeous place to be with my favorite people!
It's a great location near Chestertown. The pool was nice. The house in general is a really nice house, being seated along the river with sunset views, it was everything we'd hoped it would be.
Stayed 6 nights in Aug 2022

10/10 Excellent

David W., Arlington, VA

Liked: Cleanliness
Riverside magnificence
Perfect place for our group. Beautiful sunsets, excellent pool & comfortable house. Also loved exploring the area.
Stayed 3 nights in Jul 2022

10/10 Excellent

harpreet b.

Liked: Cleanliness
Amazing location
Stayed their with my parents , and my fried - total 9 people with two dogs . Nice and cosy and great views of the river . Rented out a boat from Chester town and enjoyed the boat rides
Stayed 4 nights in Jun 2022

10/10 Excellent

Galyna

Liked: Cleanliness
Unforgettable vocation
The house was very clean , beds comfortable. What we like the most is a back yard with a pond , beautiful nature , quit neighborhood , the pool was perfect size for 3 families , We love our stay in this property
Stayed 3 nights in Jul 2022

8/10 Good

Gayle S.

Liked: Cleanliness
Beautiful Setting
The setting was beautiful. The views of the Chester River from either sun porch or tree swing or a bench on the pier were gorgeous! Cathy, the property manager, was extremely helpful and answered every question. We were a three generation family group. Everyone enjoyed themselves. However, the futons were uncomfortable to sleep on for my adult sons. If it wasn't for the beds, I would have given it 5 stars and would be signing up for next year. Please put in real beds!
Stayed 7 nights in Jun 2022

10/10 Excellent

Kathleen S.

Liked: Cleanliness
Relaxing stay
The property was perfect for our weekend getaway. The house and yard were quiet but just minutes from town. We enjoyed feeding the ducks, fishing, and kayaking.
Stayed 4 nights in May 2022

10/10 Excellent

Yeison S.

Liked: Cleanliness
Casa de vacaciones
Muy satisfechos es una hermosa casa
Stayed 3 nights in Dec 2022