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PINE CLIFF DWELLER | 2 Bed, 2 Bath
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Entire home
Popular amenities
- Kitchen
- Washer
- Dryer
- Air conditioning
- Outdoor Space
- Parking available
Explore the area

Southport, ME
- Juniper PointPlace, Juniper Point4 min drive
- Maine State AquariumPlace, Maine State Aquarium4 min drive
- Boothbay Harbor MarinaPlace, Boothbay Harbor Marina7 min drive
- Wiscasset, ME (ISS)Airport, Wiscasset, ME (ISS)37 min drive
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About the neighborhood
Southport
With a stay at this vacation home in Southport, you'll be within a 5-minute drive of Hendricks Hill Museum and Juniper Point. .This vacation home is 2.2 mi (3.5 km) from Hendricks Head Beach and 2.4 mi (3.9 km) from Hendrick's Head Lighthouse.
What's nearby
- Juniper Point - 4 min drive - 2.3 miles
- Maine State Aquarium - 4 min drive - 2.3 miles
- Hendricks Hill Museum - 4 min drive - 1.8 miles
- Opera House at Boothbay Harbor - 7 min drive - 3.4 miles
- Boothbay Harbor Marina - 7 min drive - 3.8 miles
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
- Harborside 1901 Bar & Grill - 6 min drive
- Tugboat Inn - 7 min drive
- Footbridge Brewery - 5 min drive
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.
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.
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Conveniences include a phone, as well as a desk and a microwave.
Guests will find features like onsite parking.
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
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