[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! Waterfront vacation home with kitchen and patio ![Interior](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/8588ea51.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/a7281bd2.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Marina](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/bef35b8f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/9893caee.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008271/e13d4582.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! provides laundry facilities and more. Adventurous travelers may like the kayaking at this vacation home. Guests can connect to free in-room WiFi. 9.6 Exceptional ### Entire home 6 bedrooms4 bathrooms3500 sq ft ## Popular amenities - Parking available - Dryer - Pet-friendly - Washer - Barbecue grill - Kitchen ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### 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! 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. 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! ℠ ## Property amenities ### Beach - Beach nearby ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - 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 - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### 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 ## Similar properties ![Dining](https://images.trvl-media.com/lodging/34000000/33490000/33490000/33489984/10324cbe.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 5 bedrooms ocean view estate overlooking cape cod bay Orleans - Kitchen - Washer - Dryer - Pet-friendly 9.4 Exceptional 56 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=33489984&PinnedHotelID=33489984&HadPinnedHotel=true®ionId=-1&adults=2) ![Sun loungers](https://images.trvl-media.com/lodging/35000000/34340000/34331800/34331712/64a5b065.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home Chatham - Kitchen - Washer - Dryer - Air conditioning 10 Exceptional 101 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=34331712&PinnedHotelID=34331712&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/35000000/34080000/34077800/34077703/92c848a1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic Waterfront Home with Sweeping Chatham Water Views! 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Ocean Beach Vista! Dennis - Kitchen - Washer - Dryer - Pet-friendly 9.4 Exceptional 116 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&selected=33562838&PinnedHotelID=33562838&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 allowed Service animals are welcome, and 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 Property Registration Number C0257271260 ### Property is also known as 942753 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C41.72879%2C-69.99220&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=4aDdk3fTtnsyW5qV-2zlxpiJcUU=) Harwich, MA #### What's nearby - Nickerson State Park - 7 min drive - 5.0 km - Chatham Fish Pier - 8 min drive - 8.8 km - Chatham Lighthouse - 11 min drive - 10.2 km - Harwich Port - 11 min drive - 10.6 km - Ocean Edge Golf Club - 11 min drive - 7.8 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 vacation home is within 2 mi (3 km) of Captain's Cove Golf Course, Caleb Nickerson House, and Captains Golf Course. Chatham Marconi Maritime Center and Adventure Chatham are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus! Reviews 9.6 ### Exceptional All reviews shown are from real guest experiences. Only travellers 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.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 9.6 Cleanliness ### 9.6 Location 10 - Excellent 75 8 - Good 11 6 - Okay 2 4 - Poor 1 2 - Terrible 0 ### 10/10 Excellent #### Donna H. Jun 24, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful Location Home has lots of character and the views are beautiful. ##### Donna H. Stayed 4 nights in Jun 2025 ### 10/10 Excellent #### Kevyn G. Jul 15, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy 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! ![](https://a.travel-assets.com/ugc/hotel-reviews/8e3882d1-d187-4bc2-8b6c-e9eb2aed1bc8-1752603139293.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/d36abb15-beba-41a9-afce-1557ca66f225-1752603140203.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/fd9e9dfe-7127-47c9-84c8-6d91d96841a6-1752603140299.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/26492650-4a69-4d5b-8790-35d15ddbdddd-1752603137978.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Kevyn G. Stayed 9 nights in Jun 2025 ### 10/10 Excellent #### Treseanne A. Aug 5, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Treseanne A. Stayed 2 nights in Jul 2024 ### 10/10 Excellent #### Jake P. Jul 13, 2024 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! ##### Jake P. Stayed 3 nights in Jun 2024 ### 10/10 Excellent #### Deborah C. Oct 14, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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 ##### Deborah C. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Scott M. Jun 14, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful views The property was as advertised and clean. We thoroughly enjoyed our stay. Would highly recommend. ##### Scott M. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Susan N. Aug 28, 2024 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. ##### Susan N. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Jessica D. Aug 13, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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! ##### Jessica D. Stayed 7 nights in Jul 2024 ### 10/10 Excellent #### Kristen R. Aug 27, 2024 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! ##### Kristen R. Stayed 7 nights in Aug 2024 ### 10/10 Excellent #### Sarah L. Jul 17, 2024 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. ##### Sarah L. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Sid M. Aug 3, 2020 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. ##### Sid M. Stayed 8 nights in Jul 2020 ### 10/10 Excellent #### Jennifer R. Jul 20, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Jennifer R. Stayed 7 nights in Jul 2024 ### 10/10 Excellent #### Karen R. Jul 29, 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! ##### Karen R. Stayed 7 nights in Jul 2023 ### 10/10 Excellent #### Emily R. Sep 17, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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! ##### Emily R. Stayed 3 nights in Sep 2024 ### 10/10 Excellent #### BJ C. Aug 27, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing view We had a lovely stay ##### BJ C. Stayed 7 nights in Aug 2022 ### 10/10 Excellent #### Luke Z. Aug 1, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay! We had a great stay. The cottage is well located for water and town access and to explore the Cape. Good communication. ##### Luke Z. Stayed 7 nights in Jul 2023 ### 10/10 Excellent #### Kim R. Jul 17, 2024 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. ##### Kim R. Stayed 4 nights in Jun 2024 ### 10/10 Excellent #### Dana B. Oct 4, 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing location The best view in cape cod hands down ##### Dana B. Stayed 5 nights in Sep 2020 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent Apr 26, 2016 #### South Cottage Ideal location, amenities abound, convenient to towns.....loved it ### 10/10 Excellent #### irene b. Jun 25, 2018 #### great location and house! we loved our stay here. very roomy, enough beds for everyone and view over the water was wonderful. close to the golf courses. looking forward to staying here next year! ##### irene b. Stayed 3 nights in Jun 2018 ### 10/10 Excellent #### Sharon B. Sep 24, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Sharon B. Stayed 3 nights in Sep 2024 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Terry B. Aug 21, 2016 #### Lovely cottage on the water. We loved the property and the location on Pleasant Bay. Nice people and lots of fun sailing and kayaking. ##### Terry B. Stayed 7 nights in Jul 2016 ### 10/10 Excellent #### Mary-Anne G. Sep 20, 2023 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. ##### Mary-Anne G. Stayed 7 nights in Sep 2023 ### 10/10 Excellent #### Katie S. Oct 30, 2022 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! ##### Katie S. Stayed 3 nights in Oct 2022 ### 10/10 Excellent #### John B. Sep 5, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay at Pleasant Bay We enjoyed our second stay at this property. The house was clean and well prepared, and the view from the deck is spectacular. The property manager was very helpful and responsive. ##### John B. 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