[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Waterfront on Pleasant Bay! Vacation home in Orleans with kitchen and balcony ![Interior](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/35103b6d.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/f6f23f44.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/w2987h1990x13y0-8793d863.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/25a041b7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69330000/69320900/69320836/w2999h1995x1y0-9977ea20.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Perched on a quiet dirt road, Island Lookout: Waterfront on Pleasant Bay offers an idyllic retreat with elevated water views of Little Pleasant Bay. The newly furnished living room and kitchen/dining area are open and airy, leading out to a triangular deck that feels like being aboard a ship. With WiFi, cable TV, window A/C units in bedrooms, outdoor shower and washer/dryer you have all the comforts of home while enjoying your beach vacation. 9.0 Wonderful ### Entire home 3 bedrooms3 bathroomsSleeps 82600 sq ft ## Popular amenities - Beach view - - Parking available - Dryer - Washer - 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. ### Waterfront on Pleasant Bay! Summary: 15548 - Island Lookout: Waterfront on Pleasant Bay! The Space: At the end of a quiet road, you’ll find this piece of heaven in Orleans tucked above the trees, overlooking a large yard, and beyond that, a beautiful private beach below. As you arrive, you’ll notice a small sign for the beach path beside the driveway; you’re always just steps away from the idyllic sun drenched sand and calm waters. Entering the home brings you a level higher, and the views will amaze as soon as you enter; large bay windows open up onto a picturesque view of Little Pleasant Bay, and the ocean views are gorgeous from every room upstairs. The living room and kitchen/dining area are open, bright, and airy, and the space leads out onto a triangular deck area, which truly feels like you’re aboard a ship. To the left of the main deck area, there is a small catwalk over to a second seating area, with two rocking chairs to gaze out into the bay. Seating indoors and outdoors in between the kitchen make this a perfect entertaining space, and enjoying meals with your family and friends by the water is a nightly treat. If you do care to dine out, many options are close by on Main Street I Orleans; for breakfast try Whisk or for something more substantial, try the Rail. If you venture further, you’ll find that you can find all the provisions you need at Nauset Farms, a small local market. Back Inside the home, the master bedroom occupies the right wing of the home, complete with unbelievable water views, a king size bed, and a full en suite bathroom. Downstairs offering additional living space, plus two more bedrooms. The larger bedroom features a queen bed, and the other has two bunk beds both with twin beds. A living area and kitchenette between the two downstairs bedrooms provides a second area to relax, and can be the perfect kids living area. ​​​​​​​Take a stroll out into the grassy yard, and surrounded by large shrubs, you’ll feel remote and private. Toward the end of the yard is a pathway to the beach, and a 1 minute walk through the trees will bring you to a beautiful sandy oasis for you to enjoy; truly an ideal beach vacation. If you’re seeking something close to the beach, private, and something that really feels like a relaxing Cape Cod vacation, don’t wait to book this rare find! Home Details: \-Dogs Welcomed (w/fee of $45/night per dog) \-Sleeps 8 \-2 Floors \-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom \-Ground Floor Bedroom #1: 1 Queen Bed \-Ground Floor Bedroom #2: 2 Twin Bunk Beds (4 twins total) \-Window A/C Units in Bedrooms \-WiFi \-Cable TV \-Washer/Dryer \-Gas Grill \-Deck w/ Furniture \-Walk to Private Neighborhood Beach \-Private Yard \-Outdoor Shower \-Elevated Water Views \-Waterfront on Pleasant Bay \-Sheets and Bath Towels Provided with Beds made Upon Arrival \-Cleaned with Hospital Grade Disinfectant C0403912240 The Neighborhood: Oceanside ## Property amenities ### Beach - Beach nearby ### Internet - Available in the house: WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2.5 private bathrooms - Hair dryer - Shower - Towels provided ### Entertainment - TV with cable channels ### Outdoor areas - Balcony - Barbecue grill - Garden - Yard ### Laundry - Laundry facilities - Washer/dryer ### Work spaces - Desk - Office ### Climate control - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Near the sea ### Things to do - Water park ### 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) - Fire extinguisher ### General - Garden - Unit size: 2,600 square feet ## Similar properties ![Beach nearby](https://images.trvl-media.com/lodging/33000000/32650000/32646200/32646131/8379209c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Private Beach and Roof Top Deck! 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Chatham - Ocean view - Kitchen - Washer - Dryer 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=117356628&PinnedHotelID=117356628&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/114000000/113010000/113008300/113008269/78f075db.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus! Orleans - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=113008269&PinnedHotelID=113008269&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/33000000/32660000/32656400/32656316/c6e7fbcb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront w/ views on Blackfish Creek! Wellfleet - Kitchen - Washer - Dryer - Pet-friendly 9.4 Exceptional 32 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=32656316&PinnedHotelID=32656316&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! Pet Friendly! West Chatham - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 40 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=34077703&PinnedHotelID=34077703&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/113000000/112430000/112420600/112420558/a05f5a23.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Walk to Nauset Beach, Updated and Cozy! East Orleans - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-19&endDate=2025-10-20&selected=112420558&PinnedHotelID=112420558&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 25 ### Check-out Check-out before 9:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Rules Guest must be 25 years or older to book. Guest must sign guest agreement within 24 hours of booking. Guest must abide by the dog policy of the home... ### 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 This property accepts cash 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 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 C0403912240 ### Property is also known as 647f71e1d532e7004b05a392 House ## About the area Located in Orleans, this vacation home is near the beach. The area's natural beauty can be seen at Cape Cod National Seashore and Nauset Beach. Orleans Bowling Center and Chatham Marconi Maritime Center are also worth visiting. [Visit our Orleans travel guide](https://www.expedia.ca/Orleans.dx142149) [View more Vacation homes in Orleans](https://www.expedia.ca/Orleans-Private-Vacation-Homes.d142149-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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%7C41.74638%2C-69.97208&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=qkDxda4bsrGlZhEmlIhQPt6oXWU=) Orleans, MA ### What's nearby - Nickerson State Park - 7 min drive - 3.6 km - Skaket Beach - 13 min drive - 8.8 km - Ocean Edge Golf Club - 14 min drive - 9.6 km - Chatham Fish Pier - 15 min drive - 13.0 km - Harwich Port - 17 min drive - 14.2 km ### Getting around - Hyannis Transportation Center - 35 min drive - Hyannis, MA (HYA-Barnstable Municipal) - 32 min drive ### Restaurants - ‪Hot Chocolate Sparrow - ‬9 min drive - ‪Dunkin' - ‬9 min drive - ‪Town Cove Tap House - ‬9 min drive - ‪Hog Island Beer Co. - ‬10 min drive - ‪The Barley Neck Inn - ‬10 min drive ## Frequently asked questions ### Is Waterfront on Pleasant Bay! pet-friendly? > Yes, pets are allowed at this property. ### What time is check-in at Waterfront on Pleasant Bay!? > Check-in begins at 4:00 PM. ### What time is check-out at Waterfront on Pleasant Bay!? > Check-out is at 9:00 AM. ### Where is Waterfront on Pleasant Bay! located? > Situated by the sea, this vacation home is 2.5 mi (4 km) from Captain's Cove Golf Course and 3 mi (4.8 km) from Captains Golf Course. Orleans Bowling Center and Caleb Nickerson House are also within 6 mi (10 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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