South Orleans stay.With a stay at this South Orleans vacation home, you'll be within half a mile (1 km) of Cape Cod Beaches and 2 miles (3 km) of Captain's Cove Golf Course. Captains Golf Course and Chatham Marconi Maritime Center are also within 3 miles (5 km).
Captain's Cove Golf Course - 19 min walk - 1.0 mile
Nauset Beach - 13 min drive - 6.6 miles
Cape Cod National Seashore - 14 min drive - 9.4 miles
Hyannis Harbor - 25 min drive - 21.2 miles
Getting around
Hyannis Transportation Center - 25 min drive
Hyannis, MA (HYA-Barnstable Municipal) - 31 min drive
Restaurants
Dunkin' - 4 min drive
Three Fins Coffee House & Cacao Factory - 6 min drive
Pain D'avignon - 6 min drive
400 East - 4 min drive
Hangar B Eatery - 7 min drive
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, Beach Access, Kayaks Available Rents Friday - Friday in Peak Summer Sleeps Eight 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 one 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 $215.00 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 this site for your best selection of prime vacation homes available for summer rental on Cape Cod.
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
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
Information provided by the property may be translated using automated translation tools
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property Registration Number C0257282240
Property is also known as
942738
Frequently asked questions
How close is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! to the airport?
This vacation home is 18.1 mi (31-min drive) away from the Hyannis, MA (HYA-Barnstable Municipal) airport, the closest popular airport to the property.
Does Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! to the beach?
This vacation home is a short 8-minute walk from Cape Cod Beaches and 3.4 mi (8-min drive) from Fox Hill. Don't forget your sunscreen!
Does Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!?
No, there is no casino at this vacation home.
Is there free parking at Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!?
Free parking is not available at this vacation home.
Does Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! have a pool?
This vacation home does not have a pool.
Does Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! have a spa?
There are no spa services available at this vacation home.
How close is Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! to downtown Orleans?
This vacation home is 4.2 mi away from Orleans.
Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 4 out of 4 reviews
10 - Excellent
4
Rating 8 - Good. 0 out of 4 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 4 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 4 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 4 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Terry W.
Oct 7, 2025
Liked: Cleanliness
The views from the house were wonderful and the beach in front of the house was perfect. The house is located in the perfect spot. We are planning to go back next year.
Terry W.
Stayed 7 nights in Sep 2025
10/10 Excellent
Ted O.
Sep 24, 2025
Liked: Cleanliness
Amazing location. Lots of natural light. Would love to stay here again!
Ted O.
Stayed 3 nights in Sep 2025
10/10 Excellent
Sarah L.
Jun 20, 2025
Liked: Cleanliness
Sarah L.
Stayed 3 nights in May 2025
10/10 Excellent
Daniela L.
Jun 9, 2025
Liked: Cleanliness
We really enjoyed our stay. The location was convenient and the views from the property were exactly what we needed. We had a few minor issues during our stay that were quickly and professionally addressed by the management team.