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Waterfront, Six Bedrooms, Free Boating Bonus! 2285-H

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Interior
Miscellaneous
Interior
Exterior
Property grounds

Reviews

9.6 out of 10
Exceptional

Entire home

6 bedrooms4 bathrooms325 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Washer
  • Barbecue grill
  • Air conditioning
  • Kitchen

Explore the area

Map
Harwich, MA
  • Chatham Fish Pier
    ‪7 min drive‬
  • Chatham Lighthouse
    ‪9 min drive‬
  • Ocean Edge Golf Club
    ‪13 min drive‬
  • Hyannis, MA (HYA-Barnstable Municipal)
    ‪30 min drive‬

Room options

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About this property

Entire place

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

Waterfront, Six Bedrooms, Free Boating Bonus! 2285-H

This home is professionally managed by Pretty Picky Properties

Waterfront, Six Bedrooms, Free Boating Bonus!

NEW Listing for 2025!

Rents Friday - Friday in Peak Summer
Sleeps 11
6 Bedrooms, 3.5 Baths
Linens Included, Beds Made
Pets Considered

Location
“South Cottage” is perched on a shady bluff at the edge of 3.6-acres along Route 28 in the towns of Orleans and Harwich, belonging to Pleasant Bay Community Boating (PBCB). The Bay is directly in front of the house, so you have commanding views of the Bay and its various boating activities. Enjoy your morning coffee and your evening meals on the deck overlooking the water.

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 each.

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

Outdoor Space
The patio is the heart and soul of the property. With plenty of seating, a Weber® grill, and a constantly changing seascape, the patio will call your name to sit in a comfortable chair, dine under the open sky, and become mesmerized by the beauty of the Bay. Besides the outdoor seating, you'll find the gas grill out here, as well as the enclosed outdoor shower.
An outdoor shower is one of life's simple luxuries. This one is especially amazing, as you can shower away the day's sand and salt spray in relative privacy -- with a view of the Bay. It doesn't get much better than that!

Indoor Space
The kitchen is well equipped with a new dishwasher and plenty of glassware. The adjoining dining room can easily seat 10 for dinner. The spacious patio is accessed through the dining room for al fresco dining and taking in the view. The laundry room is just off the kitchen. South Cottage is a rambling long cottage with vaulted ceilings in all the bedrooms, but noticeably low ceilings in the dining room, kitchen and living room (6'2” – 6'4”).

Sleeping Accommodations
This property is ideal for two families or multi-generational families vacationing together, as it has two primary bedrooms -- each with a king size bed and a private full bath -- located on opposite ends of the home's main level. All bedrooms in the house have front and center views of Pleasant Bay and beyond to the Atlantic. On the second level you'll find one bedroom with a full-size double, two bedrooms with a single twin in each and the final bedroom with three twins. In all, there is sleeping for up to 11. The home has 3.5 baths.

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!
During your stay at this vacation home, you're just a quick walk from Cape Cod Beaches. The vacation home includes amenities such as free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine, and 3.5 bathrooms
  • Free WiFi (speed: 100+ Mbps (good for 1–2 people or up to 6 devices))
  • Just a 1-minute drive from Cape Cod Beaches and 13 minutes from Cape Cod National Seashore
This vacation home offers its guests barbecue grills. The front desk is open around the clock.

Property manager

Pretty Picky Properties

Languages

English

Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay
  • On the waterfront

Things to do

  • Kayak
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Swimming nearby
  • Whale watching nearby
  • Wildlife walks 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: 3,500 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

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
Property Registration Number C0257271260

Property is also known as

942753

Waterfront, Six Bedrooms, Free Boating Bonus! 2285-H Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 53 out of 64 reviews
Rating 8 - Good. 8 out of 64 reviews
Rating 6 - Okay. 2 out of 64 reviews
Rating 4 - Poor. 1 out of 64 reviews
Rating 2 - Terrible. 0 out of 64 reviews

9.6/10

Cleanliness

Reviews

10/10 Excellent

Deborah C.

Liked: Cleanliness
Wonderful views of the bay. House has everything you would need to cook. Great restaurant near by.
Very clean. Would reckon it to everyone! Great time
Stayed 3 nights in Oct 2024

10/10 Excellent

Sharon B., Hartford, Connecticut

Liked: Cleanliness
Friends Reunion
It's a wonderful cottage for a friend reunion. Seven adults were very comfortable in the space. Great table for meals, the view is wonderful, and the bedrooms plentiful. If you are not familiar with the cape, this is a good location for the bike trails, National Sea Shore (Eastham), and bay beaches. A 45 minute drive to Provincetown and 15 minutes or less to Nauset Beach. We will most certainly stay here again.
Stayed 3 nights in Sep 2024

10/10 Excellent

Emily R.

Liked: Cleanliness
Great friend reunion space!
This place was everything we could have wanted for a place to stay for a friend’s wedding. Spacious, well lit, comfortable beds. The deck is spacious and so peaceful to sit on and watch the sailors. It is a short drive to Chatham, Harwich, and Orleans. Kitchen had the essentials for cooking breakfast. Would definitely stay here again!
Stayed 3 nights in Sep 2024

10/10 Excellent

John E.

Liked: Cleanliness
Awesome place!
We had an amazing time, view and host.
Stayed 13 nights in Aug 2024

8/10 Good

Marilyn m.

Liked: Cleanliness
Pleasant bay vacay
The house was clean, pleasant, needs updating. Kitchen is older gally style. Your parking is in a short walk, but you can drop off in front of house. Property is part of community sailing camp. Beautiful view. We were given a sailing lesson which was great! Also can use kayaks a
Stayed 7 nights in Aug 2024

10/10 Excellent

Susan N.

Liked: Cleanliness
Lovely location
Location is great. The view of the bay and the sailing club is amazing . The beach is modest at best , The house was comfortable and clean and the manager very helpful. The house is old fashioned but the living space and the porch is right on the bay and great. The breeze from the bay was delightful.
Stayed 7 nights in Aug 2024

10/10 Excellent

Kristen R., Lexington

Liked: Cleanliness
Fantastic Family Reunion Week
Our extended family had a wonderful stay at Pleasant Bay Community Boating. We took advantage of the Simply Sail lesson and went kayaking in Pleasant Bay and Little Pleasant Bay. We all enjoyed just sitting on the deck watching the boats. Thank you for a great vacation!
Stayed 7 nights in Aug 2024

10/10 Excellent

Judith W.

Liked: Cleanliness
Wonderful house, fabulous view, very responsive property manager
Ten family members - ages 2- 73- stayed for one week. The location is superb for all Cape events. It is right off Rte 28. Near beaches, restaurants and convenient to Harwich, Chatham, Brewster and Orleans. Best equipped kitchen for a rental I have ever seen. The property manager is very diligent and personable
Stayed 7 nights in Aug 2024

10/10 Excellent

Jessica D.

Liked: Cleanliness
Beautiful spot
We stayed here for our wedding week and I couldn't have asked for a better place. Great spot to hang out and steps to the beach. Everything was perfect. thank you!
Stayed 7 nights in Jul 2024

10/10 Excellent

Treseanne A.

Liked: Cleanliness
Wonderful visit
The cottage is adorable and had everything our family needed for a wonderful stay. The staff of Pleasant Bay Community Boating (our hosts) could not have been more helpful. The views are just beautiful.
Stayed 2 nights in Jul 2024

10/10 Excellent

Jennifer R.

Liked: Cleanliness
Family getaway
We had an absolutely amazing week at this house. We were able to enjoy some sailing, fishing, kayaking, an amazing sunset. The views from each of the bedrooms are amazing. Property is also closely located to Orleans beaches that are amazing as well.
Stayed 7 nights in Jul 2024

10/10 Excellent

Sarah L.

Liked: Cleanliness
Awesome stay!
My friends and I had a wonderful time! We spent most of the time at the table on the beautiful porch. There isn't beach access, but we swam in the water out back which was nice.
Stayed 3 nights in Jul 2024

10/10 Excellent

Kim R.

Liked: Cleanliness
Wonderful, classic Cape Cod vacation spot
It’s not fancy, it’s not modern, but it’s a classic old Cape Cod Home with spectacular views and wonderful indoor and outdoor gathering places. The sailing lesson was a great bonus. It’s not right on a beach, but close to everything. We had a wonderful stay when we were here for a family wedding at Wequassett.
Stayed 4 nights in Jun 2024

10/10 Excellent

Jake P.

Liked: Cleanliness
Great location and property!
Close to a lot of great spots and loved being on the water. House was perfect for our group. We’ll be back for sure!
Stayed 3 nights in Jun 2024

10/10 Excellent

Scott M.

Liked: Cleanliness
Beautiful views
The property was as advertised and clean. We thoroughly enjoyed our stay. Would highly recommend.
Stayed 3 nights in May 2024

10/10 Excellent

Kathy-Lee S.

Liked: Cleanliness
MAGNIFICENT VIEW!
We had a wonderful, relaxing time- mostly on the big wrap-around deck overlooking the beautiful bay. The cottage was immaculate and we were even able to check in early! We were also very fortunate to have stayed when the majority of the time there were no events, otherwise the dock would have been very busy and we wouldn't have been able to park close to the cottage. The only real downside was finding that the refrigerator outlet didn't work- but we made do with an extension cord. Thank you very much for such an enjoyable stay!!
Stayed 3 nights in May 2024

10/10 Excellent

Caroline N.

Liked: Cleanliness
Spacious house - incredible view
We had a great time in this house and wish we could stay all summer! The house has everything anyone would need. It has a nice family and dining area for gathering, and comfortable bedrooms. The downstairs bedrooms are off to the ends of the house and are private with their own bathrooms and exterior exits. The upstairs bedrooms are comfortable. No matter where you are in the house the views are beautiful. It is close to town - a short drive. We had chilly, cloudy weather so didn’t spend anytime sitting on the nice outdoor dining area, but the house was very comfortable and the inside dining area was perfect. Definitely would go back! We’d love to do the in-season sailing on Pleasant Bay. Just a perfect Cape Cod pre-season weekend.
Stayed 4 nights in May 2024

10/10 Excellent

Sara B.

Liked: Cleanliness
Cozy House
Spacious and comfortable place, very clean. Highly recommended.
Stayed 3 nights in Dec 2023

10/10 Excellent

Mary-Anne G., Massachusetts, USA

Liked: Cleanliness
Perfect Location
Enjoyed sitting on the patio with the lovely view of the Bay just as much as we enjoyed exploring this part if the Cape. Roomy, clean, and charming.
Stayed 7 nights in Sep 2023

8/10 Good

Caren S.

Liked: Cleanliness
Girls Weekend
Had a great Girls Weekend. Huntley was so accommodating. Cottage had a lot of charm and lovely views.
Stayed 3 nights in Sep 2023

8/10 Good

Susan Y.

Liked: Cleanliness
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.

Liked: Cleanliness
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

Luke Z.

Liked: Cleanliness
Great stay!
We had a great stay. The cottage is well located for water and town access and to explore the Cape. Good communication.
Stayed 7 nights in Jul 2023

10/10 Excellent

Karen R.

Liked: Cleanliness
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

Jesse D.

Liked: Cleanliness
Beautiful little cottage on the bay
We enjoyed our stay at the sailing community because it had great views, an authentic Cape vibe, a good location, and the opportunity to sail. It is a lovely cottage that sleeps a ton of people. The ceiling height is low if you're over 6 feet!
Stayed 7 nights in Jul 2023