Perfect location on Southport Island with spectacular views, private dock & float, accessible by car or boat. Two bedroom, two bathroom, two story cottage.

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Guests 4
Bedrooms 2
Bathrooms 2
Allows Pets No


Pine Cliff Dweller is perched on the edge of a cliff overlooking Burnt and Squirrel Islands and the entrance to Boothbay Harbor and the open Atlantic! The owners of this magnificent property have maximized the view with tons of windows, covered and uncovered decks and indoor seating designed for relaxation! There is also a private dock and float for additional outdoor recreation!

Renew your spirit, breath in that clean, salt-scented breeze and feel all your cares simply melt away!

You can also pair this cottage with Piffi Biff next door for additional room! Together, they make a nice package!

Pine Cliff Dweller has a private dock and float for swimming, boating and relaxing. Bring your own boat or rent locally for kayaking, canoeing, sailing and more. Pine Cliff Dweller offers a great, easy home-base so you can be active and on the go or to simply do nothing!

From the house or the dock you can watch all manner of boats go by, from yachts to lobster boats, sail boats to dinghies; you will see it all. Porpoise, the occasional whale and migratory shore birds are all part of the view as well!

Like lobster? Connect with local lobstermen for dockside service right on your private dock!

The dining room is situated in a corner with three walls of windows overlooking the ocean, your dock and a couple islands. This is the perfect spot for morning coffee and lingering over the evening meal. Enjoy Cocktails and appetizers from the deck. The living room and family rooms are light and airy, the floor plan open and inviting. The working, wood burning fieldstone fireplace is a local tradition and adds to the ambiance. The layout of the property lends itself well to two couples traveling together with a bed and bath on each floor.

Need more room? The cottage next door, Piffi Biff, can be rented in conjunction with Pine Cliff Dweller for a mini-reunion, girls get-a-way or multi-family vacation! Due to the location and layout, this cottage is not recommended for small children.

The bedroom on the main floor has a Queen bed. There is also a futon in the family room that folds out into a double bed and a full bathroom with shower/tub combo also located on the main floor. The living room has a flat screen TV with cable and a DVD player. WiFi is available throughout the house.

The Master Bedroom is located on the second floor. A King Bed and panoramic windows overlooking the ocean make this bedroom spectacular. The en-suite bathroom has double sinks and a shower/tub combo.

1st Floor: One bedroom with a Queen bed and a family room with a Futon that folds out to a Double.
2nd Floor: One bedroom with a King bed.

1st Floor: One Full Bathroom with shower/tub combo.
2nd Floor: One Full Bathroom with shower/tub combo.

Peruse our web site for local vendors, eateries and activities. Replete with all things vacation; if you can think of it, our site most likely covers it! Be sure to reach out to us if you need any help creating the perfect vacation!

Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993.
Cottage Connection was one of the first vacation rental companies in the Mid-coast region of Maine. Jeff and Audrey Miller, who own three vacation rental homes themselves had an aha moment when they realized they could not find anyone who ‘got it’ to manager their rentals for them. Since 1993 they have been trusted by homeowners and vacationers to “connect” each family with the perfect cottage for their vacation. As Audrey puts it; “The home they stay in becomes a personality, a part of their lore when a family connects with the right cottage. Whether they want a rustic cabin in the woods or a high-end ocean bungalow, the right setting sets the tone for the entire vacation.” Learn more about how Cottage Connection can help make your vacation perfect!

The Boothbay Peninsula is a beautiful region rich in culture, history, all things nautical and of course its own unique niche in nature. The area offers ample opportunities for biking, kayaking, canoeing, fishing, charters and guided cruises, spas, golf, mini-golf, bowling, museums, antiquing, hiking and walking trails. We have the Maine State Aquarium, the Coastal Maine Botanical Gardens and the Boothbay Region Land Trust with its 30+ miles of pet friendly trails in protected areas. For a more comprehensive list of local offerings Click Here!

Southport Island is a hidden treasure on the Boothbay Peninsula. Two miles from Boothbay Harbor, you cross the bridge onto the island and feel the world change around you. You know you are on vacation. Small sandy beaches, large expanses of rocky shoreline, views of Islands and open ocean, walking, kayaking, fishing and more! This quaint and historical part of Maine is treasured by the few who know of it! From the shore you can see Cape Island once owned by Margaret Hamilton who played the Wicked Witch of the West in the Wizard of Oz. A pair of Ruby Red Slippers is on display at the Island’s library. Hendricks Head Lighthouse and Beach are just a short ride away for those who prefer swimming on more of a sandy beach. Rachel Carson frequented Southport often and mentions the area in her books. Cuckhold Lighthouse can be seen just off shore. This small little spit of land is rich in history, marine life, unique ecology and more. You will come back again and again!


Linens are included with this property
Private Dock and Float with a swim ladder
2 Small Grills, one charcoal and one gas
Fieldstone Fireplace, wood
Partially covered, Open Deck with exceptional views
Mooring Available
Flat screen TV, Cable (Basic plus other channels - e.g. HBO)
Radio/Cassette Player
Air Conditioning, Master Bedroom
Also Accessible by Boat

Can be rented in conjunction with Piffi Biff .

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Write a Review
Rufus Jones &
Mt. Pleasant, US
Reviewed: Feb 26, 2016
Property Manager
We chose Cottage Connection of Maine initially because out of the selection of available houses, they managed the one we wished to reserve. The staff has proven to be very knowledgeable and accommodating. We got good service and they offer a good selection of homes.
We come to Boothbay Harbor every summer, but Pine Cliff was by far the loveliest and most livable of the cottages we've rented in the past. Nice house, beautiful view? We've already reserved it for next year. It was so nice and clean, well kept with lovely dining room with matching china, an abundance & variety of glassware- it seemed like our our cottage for the time we were there.
Hot Springs Village, US
Reviewed: Feb 26, 2016
Property Manager
Have always been easy to work with. We are repeat guests.
We've stayed here before! Love those sunrises!! Pine Cliff Dwellers location with Perfect Views and the lobster boats purring and chugging so close by makes it hard to beat this place. Even with the rain and fog, the vistas were gorgeious.
Louisville, US
Reviewed: Feb 26, 2016
Property Manager
Cottage Connection was very helpful. Kudos to Melba.
The view was outstanding. The scenery was absolute beauty.
Mary Jane
Woodbury, US
Reviewed: Feb 18, 2016
Property Manager
Contact(s) with staff have always been pleasant. We appreciate their knowledge of rental offerings and recommendations commensurate with our needs. We have been "customers/clients" since 1996. The Cottage Connection staff is a pleasure to work with - always accommodating.
We have always found Pine Cliff Dweller very comfortable for our needs - quiet as well. Sharing the ambiance of the cottage and the area with friends from Alabama. They agreed the cottage deck and dining room are exceptional. Having stayed at this cottage many times since 1996, we were delighted to experience the terrific new deck, a new flat screen TV to view the new and weather, the new living area chair and ottoman, and the replacement front window box. To the owners of Pine Cliff Dweller, keep up the good work in your lovely new dcor!
Jean, Clark, Don & Peggy
Reviewed: Sep 30, 2014
Property Manager
Gorgeously Wonderful. Wonderful stay. We saw an eagle alight in the tallest spruce on Mouse Island and a porpoise played between the rocks and the dock.
Mary Jane
Reviewed: Jul 20, 2014
Property Manager
We have been "customers/clients" since 1996. The Cottage Connection staff is a pleasure to work with - always accommodating.
Sharing the ambiance of the cottage and the area with friends from Alabama. They agreed the cottage deck and dining room are exceptional. Having stayed at this cottage many times since 1996, we were delighted to experience the terrific new deck, a new flat screen TV to view the new and weather, the new living area chair and ottoman, and the replacement front window box. To the owners of Pine Cliff Dweller, keep up the good work in your lovely new dcor!


Check-In Day:  SaturdayJune 24-Sept 5, 2016 (Prime Season Week’s).  See below for shoulder season details.  House is only available during the shoulder season (before July and after Labor Day)

Check-In Time: BEGINS 4:00 PM during prime season

Check-Out Time:  no later than 10:00 AM

Town: Southport

Body of water:  Atlantic Ocean

Type of Waterfront: Dock & Float

Swimming Area Rating for this property is a…,   1

5 – very easy water access, sandy or pebble beach, great for all ages!
4 – Easy water access, may be a pebble beach or grassy shoreline. Still good for all ages, but young children may want water shoes.
3 – Somewhat easy water access with a rocky shoreline, or rocky bottom, not suitable for young children, but fine for older children/adults, water shoes recommended.
2 – Water access only for agile young adults or adults, rocky shoreline or bottom, may be a hill down to the water or subject to strong currents.
1 – Swimming off dock only due to a seawall or rocky/wooded shoreline,
0 – not a waterfront property.

Privacy rating for this property is a…,   3

5 – very private, secluded location, lots of protection from trees, cannot see any neighbors from the house, not close to any roads, long driveway.
4 – Private location, protection from trees, neighbors a comfortable distance away, not close to any roads.
3 – Still in a quiet location, but one neighbor close by, little protection from trees
2 – Semi-quiet location, neighbors close by, may have road noise.
1 – in-town home, little or no privacy

# of Bedrooms:  2
Bed Sizes:  (1) King (1) Queen (1) Futon opens to double

# of Bathrooms: 2
Bathroom Type: (2) Full Bathrooms on each floor

Smoking AND/OR Fireworks Are Prohibited on EVERY Property

Cottage Connection of Maine represents a wide variety of quality vacation rentals throughout the Mid Coast Region of Maine. Individually and privately owned, each vacation rental reflects the taste of its property owners. Every effort has been made to ensure that the descriptions and amenities listed are accurate. However, occasionally changes are made by the owners to furnishings, amenities and equipment. Once a change that has occurred is brought to our attention, we will update that webpage. If you have any specific questions not addressed above or are in search of specific criteria, please contact us.

In other seasons (Spring or Fall), arrival dates may be flexible, speak to the reservationist.  Also, if you book a 7 night stay in the shoulder season, a 15% discount will be applied to your weekly rate.

Linens (sheets and towels) are provided for your stay  /  Sorry, no pets allowed at this property

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