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

Top rated by guests
What a place to eat a meal on vacation
Kitchen directly off the main entrance
Kitchen off the entrance
Deck with outdoor dining
Your view from the outside shower
review stars
9.8Outstanding
(89 Ratings)
"everything was as described. The location is beautiful, and the cottage is very good. I would definitely stay here again. "
James D.
Don't miss out! Price and availability may change
9.8 / 10.0
Outstanding(89 Ratings)

House in Orleans, MA

11 guests · 6 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

This home is Professionally Managed by Pretty Picky Properties

Waterfront, Six Bedrooms, Beach Access, Kayaks Available, Pets Considered!
Rents Friday - Friday in Peak Summer
Sleeps 11
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.

Book now to lock in preferred dates.

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.

It's your vacation. Get Picky! ®

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

Non-smoking
Pets allowed
Family friendly

Map of Orleans, MA


Ratings and reviews

9.8 / 10.0
Outstanding(89 Ratings)
10.0 / 10.0Outstanding·Jul 2025
everything was as described. The location is beautiful, and the cottage is very good. I would definitely stay here again.
10.0 / 10.0Outstanding·Jul 2025
Our stay at South Cottage in East Harwich was truly spectacular. The property offers stunning water views with gorgeous sunrises and sunsets that made every morning and evening memorable.A highlight of our stay was discovering we could watch The Wequassett Resort's fireworks display right from the backyard. Experiencing the July 4th show from our own private viewing area was absolutely magical and unforgettable.The six-bedroom house comfortably accommodated our large family group and came well-stocked with essentials including shower and beach towels, kitchen amenities, laundry supplies, and beach chairs in the shed. Check-in instructions were detailed and clear, with excellent communication from property management throughout our stay.A few items worth noting for future guests: We encountered significant flies during our first few days (quickly addressed by management) and found numerous ticks on the property - typical for Cape Cod but worth being prepared for. The grill lacks an automatic igniter and can be dangerous, resulting in one guest getting burned when gas flowed too quickly before manual ignition. We reported this safety concern to management.We also experienced two major thunderstorms that knocked out power for hours each time, affecting WiFi and appliances. A backup generator would be a valuable addition for guest comfort.Management was responsive to all our concerns and documented everything appropriately. Overall this property is a Cape Cod diamond!
10.0 / 10.0Outstanding·Jun 2025
Home has lots of character and the views are beautiful.
10.0 / 10.0Outstanding·Oct 2024
Very clean. Would reckon it to everyone! Great time

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.


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