Entire home

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

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

Interior
Exterior
TV
Fridge, microwave, oven, stovetop
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Entire home

4 bedrooms2 bathrooms

Popular amenities

  • Parking available
  • Pet friendly
  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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%.

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! ℠

Property manager

Pretty Picky Properties

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Kayak
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Sailing nearby
  • Swimming nearby
  • Whale watching nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,525 square feet

Similar properties

Policies

Check-in

Contactless check-in available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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
Property Registration Number C0257282240

Property is also known as

942738

About the neighborhood

Map
Orleans, MA

What's nearby

  • Nickerson State Park - 7 min drive - 4.6 km
  • Chatham Fish Pier - 9 min drive - 9.2 km
  • Chatham Lighthouse - 11 min drive - 10.5 km
  • Ocean Edge Golf Club - 11 min drive - 7.4 km
  • Skaket Beach - 12 min drive - 9.8 km

Getting around

  • Hyannis Transportation Center - 25 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 31 min drive

Restaurants

  • ‪Chatham Pier Fish Market - ‬7 min drive
  • ‪Chatham Perk - ‬5 min drive
  • ‪Mac's Chatham Fish & Lobster - ‬7 min drive
  • ‪Corner Store- Chatham - ‬5 min drive
  • ‪Orleans Bowling Center - ‬8 min drive

Frequently asked questions

Is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! pet-friendly?

Yes, pets are allowed at this property.

Where is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! located?

Situated on the waterfront, this vacation home is within 2 mi (3 km) of Cape Cod Beaches, Captain's Cove Golf Course, and Captains Golf Course. Adventure Chatham is 3 mi (4.9 km) away.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

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

Reviews

Rating 10 - Excellent. 0 out of 0 reviews
Rating 8 - Good. 0 out of 0 reviews
Rating 6 - Okay. 0 out of 0 reviews
Rating 4 - Poor. 0 out of 0 reviews
Rating 2 - Terrible. 0 out of 0 reviews

Reviews

No reviews yet

Be the first to leave a review for this property after your stay.