South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!

This home is professionally managed by Pretty Picky Properties

Waterfront, Six Bedrooms, Free Boating Bonus!

NEW Listing for 2025!

Rents Friday - Friday in Peak Summer
Sleeps 11
6 Bedrooms, 3.5 Baths
Linens Included, Beds Made
Pets Considered

Location
“South Cottage” is perched on a shady bluff at the edge of 3.6-acres along Route 28 in the towns of Orleans and Harwich, belonging to Pleasant Bay Community Boating (PBCB). The Bay is directly in front of the house, so you have commanding views of the Bay and its various boating activities. Enjoy your morning coffee and your evening meals on the deck overlooking the water.

Based here, you are only a short drive from the village center of either Orleans or Chatham, each with a wealth of outstanding restaurants, shops and fun activities such band concerts, Cape League baseball, and much, much more. Even closer are the top-notch eateries at Wequassett Resort, including the signature Twenty-Eight Atlantic Restaurant with a Forbes 5-Star rating. If beach time is your idea of a good time, it's only a 1.3 mile drive to sandy Jackknife Cove each.

But to take advantage of this location's unique appeal, you don't have to drive anywhere. You're a neighbor of Pleasant Bay Community Boating (locally known as “PBCB”), where boating is king. There are programs and lessons for beginners as well as rentals for sailing veterans. You'll also find programs in marine science education, part of PBCB's community mission.

Outdoor Space
The patio is the heart and soul of the property. With plenty of seating, a Weber® grill, and a constantly changing seascape, the patio will call your name to sit in a comfortable chair, dine under the open sky, and become mesmerized by the beauty of the Bay. Besides the outdoor seating, you'll find the gas grill out here, as well as the enclosed outdoor shower.
An outdoor shower is one of life's simple luxuries. This one is especially amazing, as you can shower away the day's sand and salt spray in relative privacy -- with a view of the Bay. It doesn't get much better than that!

Indoor Space
The kitchen is well equipped with a new dishwasher and plenty of glassware. The adjoining dining room can easily seat 10 for dinner. The spacious patio is accessed through the dining room for al fresco dining and taking in the view. The laundry room is just off the kitchen. South Cottage is a rambling long cottage with vaulted ceilings in all the bedrooms, but noticeably low ceilings in the dining room, kitchen and living room (6'2” – 6'4”).

Sleeping Accommodations
This property is ideal for two families or multi-generational families vacationing together, as it has two primary bedrooms -- each with a king size bed and a private full bath -- located on opposite ends of the home's main level. All bedrooms in the house have front and center views of Pleasant Bay and beyond to the Atlantic. On the second level you'll find one bedroom with a full-size double, two bedrooms with a single twin in each and the final bedroom with three twins. In all, there is sleeping for up to 11. The home has 3.5 baths.

Sailing Opportunities
One sail per rental offered from mid-June through late August is a private sailing experience. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing. With your stay at Pleasant Bay Community Boating, we would like to offer this at a discounted rate of $115.00. Please reach out to the main office at least three weeks prior to your arrival at info@pbcb.cc or 508-945-7245.

Book now to lock in preferred dates.

Please enter your travel dates in the top right corner of this page for up-to-date pricing. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $195. In addition, there are state and local taxes applied to all reservations of 31 days or less that total 14.45%.

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