Private pier and pool at this waterfront Chestertown home
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
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
Great stay, comfortable for my family , overall had a great time!
5.0
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
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
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
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
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
Very positive overall.
5.0
Very positive overall.
5.0
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.
4.0
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.
5.0
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.
5.0
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.
8.0
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.
4.0
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.
10.0
Our only observation were the beds. We found them to be outdated and uncomfortable.
5.0
Our only observation were the beds. We found them to be outdated and uncomfortable.
10.0
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.
5.0
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.
5.0
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.
10.0
Perfect place for our group. Beautiful sunsets, excellent pool & comfortable house. Also loved exploring the area.
5.0
Perfect place for our group. Beautiful sunsets, excellent pool & comfortable house. Also loved exploring the area.
5.0
Riverside magnificence
Perfect place for our group. Beautiful sunsets, excellent pool & comfortable house. Also loved exploring the area.
5.0
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
5.0
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
5.0
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
5.0
Had a great stay.
Had a great stay. Kids loved the pool and fishing from the dock. Beautiful sunsets on the water. Definitely would stay again.
4.0
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!
4.0
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!
5.0
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.
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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