Square Top: 661-O

  • 4 Beds |
  • 2 Baths |
  • 8 Guests
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Description

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

To view a slide show with captions, click on icon in upper right corner of the photo.

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. 

Free Bonus: Summer guests (May 31-Sept 6) can enjoy up to five individual sails on a Sunfish sailboat and unlimited kayak uses during your stay! Your summer vacation week also includes a "Simply Sail" experience for your group with a certified instructor. Ask for details when you book.

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.  

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. 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 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%.

Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.

It’s your vacation. Get Picky!

  • Checkin Available
  • Checkout Available
  • Not Available
  • Available
  • Checkin Available
  • Checkout Available
  • Not Available

Seasonal Rates (Nightly)

Available 7-Night Min Check-In Check-Out Unavailable

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Guest Review

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Amenities

  • Enhanced Cleaning Practices
  • Cleaning Disinfection
  • Self Check In / Check Out
  • All towels and bedding washed in hot water that’s at least 60ºC
  • High-touch surfaces cleaned with disinfectant
  • Carbon Monoxide Detector
  • Fire Extinguisher
  • Smoke Detector
  • Air Conditioning (Central)
  • Air Conditioning (split units)
  • Beach Chairs
  • Beach Towels
  • Blender
  • Board Games
  • Books
  • Classic Cape Décor
  • Coffee Maker (Standard)
  • Covered Porch
  • Deck
  • Dishwasher
  • Dock
  • Fully Equipped Kitchen
  • Grill (Gas)
  • Grocery Provisioning Available
  • Hair Dryer
  • Iron/Board
  • Kayak(s) for guest use
  • Kids Toys
  • Linens Included (beds made)
  • Microwave
  • Non-Smoking Home
  • Outdoor Shower (enclosed)
  • Patio
  • Pets Considered
  • Portable Fans
  • Rents Friday to Friday during peak weeks
  • Smart TV/Apple TV
  • Toaster/Toaster Oven
  • Updated Interior
  • Updated Kitchen
  • Walk to Beach
  • Walk to Salt Water
  • Washer/Dryer
  • Waterfront
  • Water View
  • Wireless Internet (WiFi)
  • Workspace Available
  • NEW Listing for 2025

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

To view a slide show with captions, click on icon in upper right corner of the photo.

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. 

Free Bonus: Summer guests (May 31-Sept 6) can enjoy up to five individual sails on a Sunfish sailboat and unlimited kayak uses during your stay! Your summer vacation week also includes a "Simply Sail" experience for your group with a certified instructor. Ask for details when you book.

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.  

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. 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 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%.

Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.

It’s your vacation. Get Picky!

Enhanced Cleaning Practices
Cleaning Disinfection
Self Check In / Check Out
All towels and bedding washed in hot water that’s at least 60ºC
High-touch surfaces cleaned with disinfectant
Carbon Monoxide Detector
Fire Extinguisher
Smoke Detector
Air Conditioning (Central)
Air Conditioning (split units)
Beach Chairs
Beach Towels
Blender
Board Games
Books
Classic Cape Décor
Coffee Maker (Standard)
Covered Porch
Deck
Dishwasher
Dock
Fully Equipped Kitchen
Grill (Gas)
Grocery Provisioning Available
Hair Dryer
Iron/Board
Kayak(s) for guest use
Kids Toys
Linens Included (beds made)
Microwave
Non-Smoking Home
Outdoor Shower (enclosed)
Patio
Pets Considered
Portable Fans
Rents Friday to Friday during peak weeks
Smart TV/Apple TV
Toaster/Toaster Oven
Updated Interior
Updated Kitchen
Walk to Beach
Walk to Salt Water
Washer/Dryer
Waterfront
Water View
Wireless Internet (WiFi)
Workspace Available
NEW Listing for 2025
  • Checkin Available
  • Checkout Available
  • Not Available
  • Available
  • Checkin Available
  • Checkout Available
  • Not Available

Seasonal Rates (Nightly)

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Guest Review

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Rooms Details
Room Beds Baths TVs Comments
{[room.name]} {[room.beds_details]}
  • {[bd]}
{[room.bathroom_details]}
  • {[bd]}
{[room.television_details]}
  • {[bd]}
{[room.comments]}
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Including Taxes & Fees

Square Top: 661-O

  • 4 Bedrooms |
  • 2 Bathrooms |
  • 8 Guests
  • | 1 Pet

including taxes and fees
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