Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

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Entire home

Overview
Amenities
Policies
Location
Host

4 bedrooms2 bathroomsSleeps 8167 sq m

Popular amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Beach view

Explore the area

Orleans, MA

Chatham Fish Pier7 min drive
Fox Hill8 min drive
Ocean Edge Golf Club13 min drive
Hyannis, MA (HYA-Barnstable Municipal)25 min drive

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

Bedroom 4

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio

Outdoor shower

Kitchen

Separate dining area

About this property

This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for large family gatherings, and conversations blend easily through two large sliders that open onto an expansive deck overlooking the Bay. This nautical-style "Old Cape Cod" cottage sleeps 8. Two waterfront bedrooms—one with a king bed and one with a queen bed—have commanding views of Pleasant Bay. A third bedroom on the second floor sleeps two in twin beds. A fourth bedroom on the first floor has a queen bed with an adjacent first floor bathroom.

Built in 1941, Square Top commands center stage near the Northern end of an historic 3.6-acre estate, and the water’s edge is literally a stone’s throw away. Enjoy your morning coffee and your evening meals on the rustic decks overlooking the Bay. Spend your vacation beach combing, exploring the Cape and learning to sail with Pleasant Bay Community Boating (PBCB) located on this expansive property.

*Summer guests (June 15-Sept 6) can enjoy a Simply Sail experience with one of our instructors at no charge (weather permitting)! Please reserve Simply Sail 1 month in advance through our website.

*This sweet cottage--named "Square Top"--has central AC, heat and wifi. The fireplace is decorative only, and cannot be used for fires--thanks!

Property manager

Natalie Fuller

Premier Host

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Beach view

Dennis Port Vacation Rental | 3BR | 2BA | 1,800 Sq Ft | Stairs Required

Pet-friendly

Outdoor space

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 1 total)

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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

On-site parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether there is a smoke detector on the property

Property Registration Number C0163352240

We should mention

A car is required for transport to and from this property

About the area

Orleans

Located in Orleans, this cottage is on the beach. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Adventure Chatham and Orleans Bowling Center are also worth visiting. Looking to get your feet wet? Power boating, sailing and fishing adventures can be found near the property.

Orleans, MA

What's nearby

Chatham Fish Pier - 7 min drive
Nickerson State Park - 8 min drive
Fox Hill - 8 min drive
Skaket Beach - 12 min drive
Ocean Edge Golf Club - 13 min drive

Getting around

Hyannis Transportation Center - 28 min drive
Hyannis, MA (HYA-Barnstable Municipal) - 26 min drive

Restaurants

Chatham Pier Fish Market - 7 min drive
Mac's Chatham Fish & Lobster - 8 min drive
Chatham Perk - 5 min drive
Corner Store- Chatham - 5 min drive
Dunkin' - 4 min drive

Frequently asked questions

Is Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly?

Check-in begins at 4:00 PM.

What time is check-out at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly?

Checkout is at 10:00 AM.

Where is Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly located?

Nestled on the beach, this Orleans cottage is within 1 mi (2 km) of Cape Cod Beaches and Captain's Cove Golf Course. Captains Golf Course and Caleb Nickerson House are also within 3 miles (5 km).

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.0/10

Cleanliness

9.6/10

Check-in

10/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

8/10 Good

Susan Y.

23 Aug 2023

Liked: Cleanliness, check-in, communication, listing accuracy

Rest and Relaxation

This property was clean, airy and filled with light. The view of the Bay from the back of the house and deck was absolutely lovely. The house was complete in serving any kitchen, bathroom and living need we had for amenities. The central air conditioning was such relief given the unusual season of high humidity and little breeze from seaside locations. We found the property manager quick to respond to any queries we had and repairs that presented themselves. The only down side was parking off site which was an inconvenience since the Pleasant Bay Boating community used the parking in front of the cottage for parking or drop-off. Traffic and boat launch noise was at times aggravating. Overall, it did not put a dent in our overall enjoyment of this property.

Stayed 7 nights in Aug 2023

10/10 Excellent

Josh K.

9 Aug 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific Spot

We had a great time at Square Top. It was so fun being right in the middle of all the action of the community boating program. Thanks!

Stayed 7 nights in Jul 2023

10/10 Excellent

Karen R.

29 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful vacation!

This comfortable cottage with stunning views was a perfect springboard to beautiful beaches, restaurants and more. We hope to return!

Stayed 7 nights in Jul 2023

10/10 Excellent

Megan C.

5 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation - Square Top blew our expectations

The location with water access is unbeatable and conveniently located to downtown Orleans and Chatham (<10 min drive) if do decide want to leave the property. We also took a quick drive up to Wellfleet to explore. We would start our mornings bright and early down at the essentially private beach, our dog loved swimming and the shallow water allowed us to take our daughter swimming, paddle boarding and kayaking. A few other highlights:

Stayed 3 nights in May 2023

8/10 Good

Patrick P.

25 Sept 2022

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pleasant long weekend

Pretty view! Really appreciated the quick response time and accommodating spirit of property manager.

Stayed 3 nights in Sep 2022

About the host

Hosted by Natalie Fuller

In December 2014, Pleasant Bay Community Boating (PBCB) realized its dream of obtaining a permanent location on Pleasant Bay Community Boating owns two of the waterfront houses—Square Top and South Cottage-- that are available for rent to vacationers. Come stay in one of these charming Cape Cod cottages and enjoy all PBCB has to offer. PBCB is a 501(c) 3 charitable organization that was founded in 2003 by various Cape Cod boating enthusiasts who recognized the need of local families and visitors to have accessible sailing and boating opportunities in the local pristine waterways of Pleasant Bay and its tributaries. Using Flying Scots, Catboats, Sunfish and kayaks, PBCB offers lessons to students, ages 8 to 85. In addition, PBCB supplies free lessons to students in local need-based community programs and Special Olympics programs. PBCB previously operated without a permanent structure from a beach in Chatham, which was threatened by erosion and other issues. Our new permanent home is truly a dream come true. Included in your stay at PBCB, is one free sailing experience. There are two options to choose from. 1) Enjoy a two-hour afternoon or evening sailing excursion. No pressure, just enjoy the ride with one of our instructors and participate as much or as little as you like. This is a great option for those looking to practice their sailing skills, but also those looking for a relaxing boat ride. 2) For the more experienced sailors, we offer a skills assessment test. Upon passing the assessment you will be able to purchase a Pleasant Bay Pass and rent boats during our normal rental hours. Tests are on weekdays, by appointment. If you arrive on a weekend and would like to sail on Sunday, sunfish are available. We strongly recommend you book your sailing experience in advance of your stay. Weather depending, Kayaks can be taken out free of charge: 830am to 330pm, Monday to Friday. 100pm and 330pm Saturday and Sundays

Why they chose this property

Square Top on Pleasant Bay.... is the perfect setting for making Cape Cod memories—learn to sail from certified instructors, kayak on protected waters, enjoy quiet moments gazing over a constantly changing canvas, spend time with family and friends. Pleasant Bay is the jewel of Cape Cod. Enjoy its beauty from the best vantage point on the Bay.

What makes this property unique

Unfurl your sails and set a course for adventure on Pleasant Bay!
The 3.6-acre historic McClennen compound on Pleasant Bay—complete with four waterfront houses, a dock and a boathouse—has been home to sailors, beachcombers and admirers of the Bay for generations. Now owned by Pleasant Bay Community Boating (PBCB), this historic property remains intact, and the tradition lives on! You and your family and friends now have the unique opportunity to live on the banks of Pleasant Bay while learning to sail!
Your summer vacation week includes a "Simply Sail" experience for your group with a certified instructor. Please sign up for boating experiences 1 Month in advance with our sailing coordinator (508-945-SAIL). Don't delay, as lessons tend to fill up fast.