Entire home

South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!

Waterfront holiday home with kitchen and patio

Photo gallery for South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!

Outdoor dining
View from the back deck
Shared access to a dock
Outdoor dining
Water views from your dining room!

Reviews

9.6 out of 10
Exceptional
6 bedrooms3+ bathroomsSleeps 11325.2 sq m

Popular amenities

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

Explore the area

View map
Harwich, MA
  • Place, Chatham Fish Pier
    ‪7 min drive‬
  • Place, Chatham Lighthouse
    ‪9 min drive‬
  • Place, Ocean Edge Golf Club
    ‪11 min drive‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪25 min drive‬

Rooms & beds

6 bedrooms (sleeps 11)

Guest Bedroom #1

1 King Bed

Guest Bedroom #2

1 Double Bed

Guest Bedroom #3

1 Single Bed

Guest Bedroom #4

1 Single Bed

Guest Bedroom #5

3 Single Beds

Primary Bedroom

1 King Bed

3 bathrooms, 1 half bathroom

Guest Bathroom

Toilet · Shower only

Guest Bathroom

Bathtub · Toilet

Powder Room

Toilet

Primary Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!

This home is professionally managed by Pretty Picky Properties

Waterfront, Six Bedrooms, Free Boating Bonus!

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.

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.

Sailing Opportunities
One sail per rental 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 $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 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! ℠

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number C0257271260

About the area

Harwich

Located in Harwich, this holiday home is on the waterfront. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Chatham Marconi Maritime Center and Adventure Chatham are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Harwich, MA

What's nearby

  • Nickerson State Park - 7 min drive - 5.6 km
  • Chatham Fish Pier - 7 min drive - 9.2 km
  • Harwich Port - 9 min drive - 10.6 km
  • Chatham Lighthouse - 9 min drive - 10.2 km
  • Ocean Edge Golf Club - 11 min drive - 9.5 km

Getting around

  • Hyannis Transportation Center - 25 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 30 min drive

Restaurants

  • ‪Three Fins Coffee House & Cacao Factory - ‬6 min drive
  • ‪Dunkin' - ‬4 min drive
  • ‪Pain D'avignon - ‬6 min drive
  • ‪Hangar B Eatery - ‬7 min drive
  • ‪400 East - ‬4 min drive

Frequently asked questions

Is South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! pet-friendly?

Yes, pets are allowed at this property.

Where is South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! located?

Situated on the waterfront, this holiday home is within 2 miles (3 km) of Cape Cod Beaches, Captain's Cove Golf Course and Caleb Nickerson House. Captains Golf Course and Chatham Marconi Maritime Center are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 75 out of 89 reviews
Rating 8 - Good. 11 out of 89 reviews
Rating 6 - Okay. 2 out of 89 reviews
Rating 4 - Poor. 1 out of 89 reviews
Rating 2 - Terrible. 0 out of 89 reviews

9.6/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Jake P.

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

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

Sid M.

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

Pleasant stay on Pleasant Bay

Ample space for a family of 6 adults and a child; beautiful location with amazing views of Pleasant Bay; nice location and helpful staff. Thoroughly enjoyed our stay.
Stayed 8 nights in Jul 2020

10/10 Excellent

Susan N.

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

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

BJ C.

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

Amazing view

We had a lovely stay
Stayed 7 nights in Aug 2022

10/10 Excellent

Sarah L.

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

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

Kristen R.

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

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

Kim R.

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

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

Katie S.

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

Lovely weekend retreat

The house was perfect for our group of 10. Cozy and comfortable with an amazing view and great location. Huntley was a great host. Would definitely stay again!
Stayed 3 nights in Oct 2022

10/10 Excellent

Mary-Anne G.

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

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Elena A.

This is a charming, cozy summer cottage with an incredible view of Pleasant Bay!

This charming, cozy summer cottage has a beautiful view of Pleasant Bay and was a relaxing place to take a vacation. It's close to Chatham town center and the beaches. We had a great time and look forward to more family memories there again in the future!
Stayed 3 nights in Jul 2016

10/10 Excellent

USHA T.

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

Gorgeous Views

This house is located in a lovely area of Cape and has beautiful views. It is perfect for a large family.

10/10 Excellent

Jennifer P.

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

Pleasant Bay

Our group of 8 spent a week in the South Cottage in early July. There was plenty of space, the property was extremely clean and the location was within 10 min of everything we wanted to do. I highly recommend staying here.
Stayed 7 nights in Jul 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Eric B.

Beautiful view

Would have been nice to have the beds made but otherwise everything was spectacular
Stayed 4 nights in Aug 2017

10/10 Excellent

Ilene M.

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

Beautiful spot on Pleasant Bay

A lovely well appointed cottage, with low ceilings as mentioned in the listing. We were there in the off season so it was quiet with lots of opportunity to sit outside and enjoy the beautiful view.
Stayed 3 nights in Oct 2022

8/10 Good

Marilyn m.

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

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

8/10 Good

Patrick P.

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

10/10 Excellent

Sarah L.

Liked: Cleanliness, communication, location, listing accuracy

Fantastic Location on Pleasant Bay

This is a wonderful house right on Pleasant Bay. It is very comfortable, clean, and convenient. Being part of PBCB is a tremendous benefit for anyone interested in sailing and/or kayaking. Beautiful dock. Great swimming. The staff is friendly and accommodating.
Stayed 4 nights in Jun 2019
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Carole S.

loved it!

Great location, great setting. Excellent space to all be together for meals and to hang out. Stunning view. Excellent access to sailboats and small beach. We really liked having our own beach in our "backyard". The kids AND the grownups loved all of it.
Stayed 4 nights in Sep 2017

10/10 Excellent

Carly Z.

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

Loved it!

Sunrise was amazing!!! Property was quaint and homey. I will be back! Great way to unwind!
Stayed 3 nights in Sep 2021

10/10 Excellent

Debra B.

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

Great views

I stayed with 7 family members in this cute and clean cottage. The views of the bay are amazing and we loved the sounds of the water and boats. We were able to use some kayaks from the property. The kitchen was good for quick meals. The parking in a separate lot was not a problem since we could still do drop offs and pick ups right outside.
Stayed 7 nights in Jun 2022

8/10 Good

Paul S.

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

Comfortable house in a beautiful spot

Everything went smoothly and everyone was easy to deal with. For our needs the location was not ideal because you can't safely walk or bike from the house except out to the dock. The traffic on Route 28 is too fast.
Stayed 3 nights in Sep 2019

8/10 Good

Roslin M.

Enjoyed being on Pleasant Bay

We loved our two week stay, especially our granddaughter who took sailing lessons for a week. The view is spectacular. Our only reservation was the closenest to the road. It was not safe to walk along or bike on. We enjoyed the cottage and the property manager was very helpful with things that needed attention, like a sliding door and chairs that needed to be glued. The sunrises and fog on the water made everything worthwhile.
Stayed 14 nights in Aug 2018

10/10 Excellent

Carol D.

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

Loved it!

We had a great stay at South Cottage. Management is very responsive and welcoming; the house was clean and very nicely furnished with lots of comfortable spaces. Our 3 generations had plenty of space to spread out, as well as to hang out together. The weather was perfect, so we didn't need to explore the ample supply of games, puzzles and books. Lots of dishware, utensils, and pots and pans in the kitchen. We cooked many fish dinners! The bay is beautiful and calming. The "kids" (young adults) swam, went sailing and kayaking, and took advantage of area beaches. Great vacation - we didn't want to leave!
Stayed 6 nights in Jun 2021
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Vidyasagar K.

Wonderful, quiet, roomy, quaint and with a patio for gorgeous sunsets!

Gorgeous old house filled with character with multiple bedrooms and bathrooms, all of which are lovely. Very private with lovely hosts who checked in on us to make sure all was well, and then let us do our own thing. Fantastic open common room with an amazing view. Patio has lots of tables and chairs and a clear view of the bay for watching sunrise and sunset. Fully equipped kitchen : we cooked each night for 8 adults and one child, no shortage of cookery or crockery. Great beaches and biking are minutes away. Charlie, Huntley and Abby will hook you up with kayaks (use anytime 9-4) or sailing lessons which we enjoyed thoroughly. Our lab group had an amazing, relaxing and restorative time and we will be back next year! Thanks to the PBCC crowd for a delightful time.
Stayed 4 nights in Jul 2017

10/10 Excellent

Scott B.

Nice Cape experience and georgous views.

Many thanks to Natalie for her efforts in accommodating our last minute reservation. The staff at Pleasant Bay Community Boating also bent over backwards for any request we had. I was hoping for a nice Cape experience for my family and we got it. The cottage is a good central location to explore the Cape. We were able to visit both Provinceton and Hyannis Port. We’re not boaters but we so enjoyed watching the sailboats criss cross the bay in the gentle breeze. I even watched a seal feed on a large school of fish while standing on the dock at daybreak, he literally swam right under me-priceless. I would very much recommend. The front of the home is right on a somewhat busy road and the living quarters are “rustic” but the views, boating vibe and courteousness of Natalie and Huntley made it a great memory for my family.
Stayed 3 nights in Jul 2018

About the host

Hosted by Pretty Picky Properties

Host profile image
There are a lot of places to rent for a summer vacation on the Cape. There are only a few Pretty Picky Properties. Most are directly on or very near the beach. Our homeowners love their properties, fastidiously maintain them, and expect guests to treat them accordingly. Our guests demand a prime location and a vacation experience that far exceeds the typical Cape summer rental.

When you spend a good amount of money for a perfect summer vacation, you want to be sure before you commit. That's why we take the time to carefully and completely answer all your questions by phone or email. If you can visit the Cape in advance, we'll be happy to show you one or more properties you're considering.

Most guests are also comforted to know that Pretty Picky also has a property management division. Most unforeseen property issues can be resolved quickly with our ready access to maintenance resources.

We look forward to helping you plan your ideal Cape Cod vacation!

The Pretty Picky Team

Languages:

English

Premier Host

They consistently provide great experiences for their guests