Private pier and pool at this waterfront Chestertown home | House in Chestertown

Q: How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $1,166 per night with includes Security/Safety, Breakfast, Child Friendly, Internet, Kitchen, Air Conditioner, TV, Private Pool, Oceanfront, Guest Services, Parking, Sports/Activities, Laundry, Bedding/Linens, Wellness Facilities, Pet Friendly, Pool, Ocean View, Balcony/Terrace, Spa, Fireplace/Heating, View with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

9.8 (22 Reviews) | Pet Friendly 4 Bedrooms 3 Bathrooms 10 Guests

Chestertown House | Private pier and pool at this waterfront Chestertown home

4 Bedroom House in Chestertown

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.
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 4 Bedrooms and 3.5 Baths. There is Master en-suite bedroom on the Main Floor, 3 bedrooms and a combined Den/bedroom and 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!
4 Bedrooms/3.5 Baths; sleeps 10 adults
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
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

Private pier and pool at this waterfront Chestertown home is located in Chestertown. Private pier and pool at this waterfront Chestertown home provides accommodation, featuring Bedding/Linens, Wellness Facilities, Pet Friendly, among other amenities. This House features Bedding/Linens, Wellness Facilities, Pet Friendly, to make your stay a comfortable one.

Private pier and pool at this waterfront Chestertown home has 4 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

Amenities

Air Conditioner
Parking
Pet Friendly
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Spa
Fireplace/Heating
Guest Services
Breakfast
Child Friendly
Internet
Kitchen
Laundry

Policies

Event Policy No events allowed

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

Child Policy Children are welcome.

Pet Policy Pets allowed service animals are welcome, and are exempt from fees

Smoking Policy Smoking is not permitted

Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

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Reviews

Taraa W. Oct 11, 2023 09:52:03 PM

Summary: 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 .

Jonathan b. Sep 28, 2023 01:53:51 AM

Summary: Great stay, comfortable for my family , overall had a great time!

Sep 22, 2023 06:46:06 AM

Summary: 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!

Malcolm E. Aug 6, 2023 10:15:57 PM

Summary: 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

Mary S. Aug 6, 2023 11:01:26 AM

Summary: 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.

Bill H. Jul 12, 2023 09:26:30 AM

Summary: 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!

Brewster F. Jul 9, 2023 11:01:41 AM

Summary: Very positive overall.

Jen L. May 25, 2023 01:16:53 AM

Summary: 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.

Sheri P. May 16, 2023 08:32:36 PM

Summary: 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.

Rosario L. Jan 12, 2023 10:11:34 AM

Summary: 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.

FAQ's

Is this Chestertown house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestertown house have a swimming pool?

Yes, this Chestertown house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $1,166 per night with includes Security/Safety, Breakfast, Child Friendly, Internet, Kitchen, Air Conditioner, TV, Private Pool, Oceanfront, Guest Services, Parking, Sports/Activities, Laundry, Bedding/Linens, Wellness Facilities, Pet Friendly, Pool, Ocean View, Balcony/Terrace, Spa, Fireplace/Heating, View with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Chestertown house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestertown house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestertown house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestertown house?

Based on the information reported by the owner or manager, the Chestertown house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestertown house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check House Availability

Nightly rates from:

US $1,166