Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!

This home is professionally managed by Pretty Picky Properties

Spectacular Pleasant Bay Views, Free Boating Bonus!

NEW Listing 2025!

Rents Friday - Friday in Peak Summer
Sleeps Eight
Four Bedrooms, Two Baths
Linens Included, Beds Made
Pets Considered

Location
If you've ever driven on Route 28 between Chatham and Orleans, you were no doubt struck by the stretch of that road that runs right by beautiful Pleasant Bay. That's the view you get from this property, definitely one of the most scenic water views on all of Cape Cod. 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 Beach.

But to take advantage of this location's unique appeal, you don't have to drive anywhere. You're right next door to 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.

Outside Living Space
Given the stunning view from here, you'll no doubt choose to spend most of your time on this cottage's oversized deck where the entire panorama of Pleasant Bay is on display for you. Besides the outdoor seating, you'll find the gas grill out here, as well as the enclosed outdoor shower. The patio offers another attractive outdoor gathering place. Just steps from the cottage, you also have access to a small private beach and an extra-long dock, each of which is shared with PBCB.

Inside Living Space
The home's main level presents an appealing, open concept floorplan which flows from the fully equipped, updated kitchen with a big gas range into the spacious living room and dining area. This entire space is open, bright and cheery, thanks to a virtual wall of glass showcasing that breathtaking water view. A handsome beamed ceiling adds to the cottage charm. There's a second lounge area here as well. The main level is home to one of the cottage's two full baths, as well as the laundry/pantry, including a full-size spare fridge.

Sleeping Accommodations
There's one main level bedroom, which has a queen size bed and its own private full bath en suite. The rest of the sleeping is provided on the second level. You'll find a king bedroom, another queen and a third bedroom with a pair of twins. The king and queen bedrooms on the second level have commanding, elevated water views.

Sailing Opportunities
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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