40-OC Waterfront Compound, Sleeps 16, Big Pool, Pickle Ball
Orleans Vacation Rental - ID 37743

New Listing for 2023!

Sleeps 16
Rents Friday to Friday in Peak Summer
Linens Included, Beds Made


This property and its guests are protected by: Extra Steps Cleaning & Prep. Please ask for details.

Formerly the Pleasant Bay Sailing Camp, this stunning 2.4 acre, two-dwelling property overlooking Little Pleasant Bay has been transformed by its owners into an enchanting vacation compound for your group of up to 16.

Launch kayaks from the private beach and explore the gentle waters of the bay. Partner up for pickle ball or tennis on the private court shared with only one neighbor. Swim laps or just float the day away in the large heated and covered pool. Drive just 10 minutes to Orleans center, 15 to Chatham, either offering destination dining, shopping, and entertainment, including Cape Cod League baseball. 

Both the main house and guest cottage have large decks, and plenty of lounge seating to enjoy the views. The main house deck offers two large, umbrella-shaded tables with plenty of seating for your waterfront dining. Here’s where you’ll find the enclosed outdoor shower and the gas grill.

Inside the main house you’ll be impressed by the size of the rooms and the open and social common space. The fully equipped main house kitchen provides topline appliances, granite counters, including an oversized island with counter seating for four. The adjoining dining room seats 10 and presents a superb water view. There’s a wet bar and wine fridge here as well. You have plenty of lounge seating in the living room, including double sofas. You’ll enjoy the big smart frame TV, which doubles as wall art until you’re ready to tune in.

The main level is also where you’ll find the first primary bedroom suite with its king size bed, en suite private bath with a step-in shower and double sink vanity.  You can walk out to the deck from the primary as well. The main level also includes the laundry and another full bath. 

The second level loft area is home to the regulation size pool table with its classic sock pockets. There are two full-size double beds on this level. 

Take the second stairway to find a third bedroom, really a second primary suite with a king size bed and private full bath with dual vanity. Go up another half level and you’ll discover an office workstation for anyone in your group who needs to work remote part of the time. There’s also a kitchenette on this level, as well as another big TV.

The main house offers still more living space on the lower level. There’s two more bedrooms each with three twins. You’ll find another full bath here plus a media room.

The guest cottage is located at the rear of the property for total privacy. It has a good-sized deck with a great view of the tennis/pickle ball court. Inside you’ll find a full kitchen, dining table for six and a full bath with a shower plus a stackable laundry. The living room has two couches and a large smart TV. There are two bedrooms here, one with twins, one with a queen.

This property has high speed Wi-Fi, a Sonos® sound system, cable/smart TV, and air conditioning via split units in virtually every room for customized cooling.

Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $225. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.
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Nearest beach: 2.1 mi to South Orleans Beach and Waterfront on Little Pleasant Bay