Title: PINE CLIFF DWELLER | 2 Bed, 2 Bath - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=19129326&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # PINE CLIFF DWELLER | 2 Bed, 2 Bath Vacation home in Southport with kitchen and patio ## Photo gallery for PINE CLIFF DWELLER | 2 Bed, 2 Bath ![Terrace/patio - PINE CLIFF DWELLER | 2 Bed, 2 Bath (Southport)](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129326/bafc7b2e.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior - PINE CLIFF DWELLER | 2 Bed, 2 Bath (Southport)](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129326/d9c77c1d.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, desk, iron/ironing board, WiFi - PINE CLIFF DWELLER | 2 Bed, 2 Bath (Southport)](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129326/73753bd7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, fireplace, DVD player - PINE CLIFF DWELLER | 2 Bed, 2 Bath (Southport)](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129326/7ab50d1a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - PINE CLIFF DWELLER | 2 Bed, 2 Bath (Southport)](https://images.trvl-media.com/lodging/20000000/19130000/19129400/19129326/c5862114.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Perched on a cliff overlooking the ocean and islands, Pine Cliff Dweller offers a memorable Maine vacation retreat. Enjoy morning coffee or evening meals in the dining room with three walls of windows, cocktails on the open deck, and cozy nights by the wood-burning fireplace. With WiFi throughout, cable TV in the living room plus washer/dryer in master suite bathroom this home is perfect for relaxation seekers and adventurers alike. ### Entire home 2 bedrooms2 bathroomsSleeps 41 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Air conditioning - Outdoor Space - Parking available ## 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. ### PINE CLIFF DWELLER | 2 Bed, 2 Bath Pine Cliff Dweller: Classic Coastal Comfort and Panoramic Views Perched on a cliff overlooking the entrance to Boothbay Harbor and the islands of the Atlantic, Pine Cliff Dweller is a treasured family home ready for your next memorable Maine vacation. This cozy, traditional cottage serves as a popular home base for both adventurers and those seeking a quiet retreat, offering a warm and inviting atmosphere that feels like a true home away from home. Charming Features Panoramic Ocean Vistas: Watch the world go by from the dining room, which features three walls of windows overlooking the ocean, your private dock, and surrounding islands. Classic Maine Ambiance: Enjoy the cozy feel of this non-minimalist retreat, complete with a working, wood-burning fieldstone fireplace that serves as the heart of the home. Master Suite with A/C: The second-floor master bedroom features a king bed, panoramic views, and air conditioning to ensure comfort on warm summer nights. Private Dock and Float: Witness the activity of the harbor firsthand, from elegant yachts to hardworking lobster boats. You may even spot porpoises, migratory shorebirds, or the occasional whale. Love fresh seafood? You can connect with local lobstermen for dockside service right on your private dock! Inviting Living Spaces: The open layout is filled with natural light thanks to large windows and sliding doors, making it easy for guests to gather in the family room or living area. Perfect for Groups: With a bedroom and full bathroom on each floor, this home is ideal for two couples or small families. For larger gatherings, the neighboring cottage, Piffi Biff, can be rented in conjunction for a multi-family getaway. The Details: Minimum Stay: Weekly (Saturday-Saturday) during June, July, and August; 4-night minimum in the Fall. Stay for a week or longer during the Fall to receive a better value on your booking! BEDROOMS: (1) King (Master with A/C), (1) Queen. BATHROOMS: (2) Full bathrooms, both featuring tub/shower combinations. DOGS PERMITTED? No, pets are not allowed at this property. LINENS & TOWELS INCLUDED? Yes, linens and towels are included in your reservation. Explore the Region Southport Island Exploration: Discover the quiet charm of the island, including the Southport General Store, Hendrick's Head Beach, and the scenic views along the shore. Iconic Sightseeing: From the cottage, you have a front-row seat to views of Burnt Island and Squirrel Island. Boothbay Harbor Entrance: Enjoy being at the gateway of the region's most famous harbor, just a short drive from downtown shops and restaurants. Book your classic Maine retreat at Pine Cliff Dweller today! COTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993\. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage. ## Property amenities ### Internet - Available in the house: WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Microwave - Oven - Refrigerator - Stovetop ### Bedrooms - 2 bedrooms - Bedsheets provided - Sofa bed ### Bathroom - 2 bathrooms - Bathtub - Hair dryer - Towels provided ### Living spaces - Fireplace ### Entertainment - DVD player - TV with cable/satellite channels ### Outdoor areas - Barbecue grill - Patio ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board - Phone ### 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: 1 square foot ## Similar properties ![Beach](https://images.trvl-media.com/lodging/34000000/33510000/33501100/33501002/2084562d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Boothbay Open Plan 1- Bedroom Apt. 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Southport - Kitchen - Parking available - Microwave - Living/Dining area 9.8 Exceptional 6 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=33501002&PinnedHotelID=33501002&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/35000000/34880000/34875600/34875583/90357a7f.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Decker Cove Southport Paradise with Central Air Conditioning Southport - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 20 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=34875583&PinnedHotelID=34875583&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33710000/33703600/33703534/9a585917.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Classic Boathouse - 2BD Waterfront Cottage - Dock & Float Access Southport - Kitchen - Pet friendly - Outdoor Space - Parking available 9.4 Exceptional 20 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=33703534&PinnedHotelID=33703534&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby](https://images.trvl-media.com/lodging/34000000/33980000/33974300/33974280/c9b7ebc0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 3 Bedroom Classic Maine Cottage, Close To Beach Southport Island - Ocean view - Kitchen - Washer - Dryer 9.6 Exceptional 27 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=33974280&PinnedHotelID=33974280&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-02-13&endDate=2026-02-14&selected=19129326&PinnedHotelID=19129326&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=19129326,33501002,34875583,33703534,33974280) ## Policies ### Check-in Check-in time starts at 5:00 PM Contactless check-in available Minimum check-in age: 30 ### 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 Information provided by the property may be translated using automated translation tools ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events 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 Parties and events are allowed on site 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 is also known as 75cec5d8-0280-48c1-a716-3360f2d95dba ## About the area Southport is home to this vacation home. Hendricks Head Light and Boothbay Harbor Memorial Library are local landmarks, and the area's natural beauty can be seen at Ovens Mouth Preserve and Hendricks Head Beach. Maine State Aquarium and Coastal Maine Botanical Gardens are also worth visiting. [Visit our Southport travel guide](https://www.expedia.ca/Southport.dx183298) [View more Vacation homes in Southport](https://www.expedia.ca/Southport-Private-Vacation-Homes.d183298-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%7C43.82996%2C-69.64907&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=rsu2O5UOBhNiRjP8r5zoRYTXcNw=) Southport, ME ### What's nearby - ![Boothbay Harbor Maine](https://images.trvl-media.com/place/6186217/beecd738-62a0-40fa-96f1-5f28f019cb34.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Boothbay Harbor Marina 7 min drive \- 6.2 km - Juniper Point 4 min drive \- 3.6 km - Maine State Aquarium 4 min drive \- 3.6 km - Hendricks Hill Museum 4 min drive \- 2.9 km - Opera House at Boothbay Harbor 7 min drive \- 5.4 km ### Getting around - Brunswick Station 51 min drive - Wiscasset, ME (ISS) 33 min drive ### Restaurants - Circle K 7 min drive - Pinkham’s Gourmet Market 7 min drive - Tugboat Inn 7 min drive - Harborside 1901 Bar & Grill 6 min drive - Boothbay Lobster Wharf 8 min drive ## Frequently asked questions ### Is PINE CLIFF DWELLER | 2 Bed, 2 Bath pet-friendly? ### How much is parking? ### What time is check-in at PINE CLIFF DWELLER | 2 Bed, 2 Bath? ### What time is check-out at PINE CLIFF DWELLER | 2 Bed, 2 Bath? ### Where is PINE CLIFF DWELLER | 2 Bed, 2 Bath located? ## Have a question? 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