LOCATION: Southport Island, Boothbay Harbor - Great Views On Boothbay Harbor

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Guests 12
Bedrooms 5
Bathrooms 3
Allows Pets Yes
Property Size 2,500 sq. ft.

Property Info


Main Cottage: Kitchen, Dining Area that can accommodate 12, Living Room, Sitting Room with TV, Master King Bedroom (new mattress for 2017) with  en suite stall shower bathroom, King Bedroom, Bedroom with 2 Twins, Shared Bathroom with stall shower, Laundry, Enclosed Screen Porch , Outside shower 

Barn: Kitchen, Living Room, Bedroom with King Bed, Bedroom with two twins, Loft with a Full bed and two twins, Full Bathroom with Claw foot Tub, Deck, Outside shower.

DOGS PERMITTED? Dogs are considered at this property. All dogs must first meet our Pet Guidelines to be considered. J1

An awesome vacation spot for a large family group! Looking right into Boothbay Harbor, this cottage is located in the best spot for kayaking and boating as well as all the best that Boothbay Harbor offers. The cottage is actually just across from Boothbay on Southport Island as noted in the maps below.

The property is located on a quiet narrow road so although the road separates the cottage and barn, even the youngest of children can safely walk across the road between the two. The bathrooms in the main cottage were renovated in 2014. Air conditioning was also added to the main home. Enjoy the gourmet kitchen (for a cottage) and the great dock and deck overlooking the water.

Robinson's Wharf - Which has the Restaurant & Tug Pub, a Gift Shop, and Seafood Market, as well as an ice cream stand, is within a short half mile walk from this property.


BOATS INCLUDED? None. Further, our sister company Maine Watercraft Rentals, Inc. does NOT service the Boothbay area.  Kayaks, Stand-Up-Paddle boards and even bicycles are offered for rent through Tidal Transit Kayak Tours & Rentals. Their website with contact information is located by clicking HERE.  For Power and Sail boats, check out West Harbor Recreation by clicking HERE

CLEANING FEE & LINEN/TOWEL RENTAL FEE: Yes, a cleaning and linen/towel towel rental fee of $400 per rental applies.  VIP Towels are included at this rental.  Guests may add additional towels or bed linens through the reservation process.  Learn more about our linen & towel rentals on the Rental Guidelines Page of our website.  Guests may reduce this fee to $200 if they choose to bring their own bed linens and towels.

SECURITY DEPOSIT: No, the owner of this property does not require a security deposit, however, guests are still financially responsible for non-accidental damages at the property.

OFF-SEASON PRICING: In order to make some of our larger or "Elite" properties more attractive to smaller groups in the Off-Season, we`ve created a Custom Pricing Option. Pricing for rentals that occur in the advertised Off Seasons (1/1/17 - 6/17/17 & 9/2/17 - 12/31/17)  for this property are based on 4 people staying only in the main cottage. Additional people, up to the maximum allowed for the property, will be charged an additional $175 per person - per week if a rental occurs in these time-periods.  After 6 people, the barn will be included. Guest must select this option during the reservation process.

Linens & Bath Towels: See above under 'Cleaning & Linen/Towel Fee'
Cleaning: The property will be professionally cleaned before and after the rental assuming the average 6 hour cleaning is needed. Above normal cleaning charges will be billed to Guest at $30 per hour
Outdoor Showers: Yes, one at the barn, and one at the cottage
Washer & Dryer: Yes
Dishwasher: Yes
Coffee Maker: Yes, Combination standard automatic drip with filters and K-Cup
Air Conditioning: Yes - The main cottage has an AC system in the bedrooms and living area.  Fans are located throughout the property as well.  Please note many of the windows in the cottage do not open well or at all - the previous Owners invested in AC instead of repairing many of them.  Still at least several windows do open.
Heat Source: Wall-Mounted Mini Splits in Cottage
Internet Access: Yes, with Wi-Fi in the main house (there is no internet access in the Barn)
TV: Smart TV with DVD, Cable, and Netflix access (BYO password) in the Main Cottage & TV with DVD player only (no cable service) in the Barn.  TV Instructions for the Cottage are located here.
Water Source: Town Water (okay to drink from tap)
Grill: Propane Gas Grill
Outdoor Firepit: No
Usable Fireplace: No
Closest Shopping Village: Boothbay Harbor, 2.5 miles
Number of Restaurants within 5 Miles: 25 Plus
Water Frontage: Yes
Beach Access: No, public 2 miles away
Dock/Pier Access: Yes
Boat Mooring: Yes - for boats up to 35 feet long - PLEASE CHECK WITH US before bringing a boat to the property.
Property Good For Fisherman: Yes
Additional Amenities: Minimum Standards List

Google Map


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Write a Review
West Hartford, US
Reviewed: Aug 5, 2017
Property Manager
Well run operation
Awesome place. We stayed 2 weeks here summer of 2016 and returned for another 2 weeks this year. Our favorite features: the dock and mooring are protected from ocean swell but big enough for our 27 foot boat, perfect location from which to launch island adventures or trips to town. The views toward town from master BR, kitchen table, deck and porch are amazing, especially at sunset. It's the right blend of cottage and comfortable thanks to nicer kitchen and AC. Barn offers guest quarters and lots of parking.
Crozet, US
Reviewed: Sep 25, 2016
Property Manager
Very easy interaction.
The Pine Cliff cottage has a great, sweeping view of Boothbay Harbor and Mouse Island. We saw seals a few times at high tide in late September. Bring your binoculars!
Lansdale, US
Reviewed: Sep 10, 2016
Property Manager
We have used this agency many times and find them thorough, reliable and easy to work with.
This house is a gem! Lift your head from the master bedroom pillow early enough and you are treated to stunning sunrise views. Then rush into the small but very well equipped kitchen to grab a cup of coffee. You have a choice of a great dining room table to catch the rest of the sunrise, or better yet you have a choice of 2 decks plus a dock to catch the rest of the sunrise views. This a fairly private location with fabulous harbor views but close enough to the boothbay harbor action. As other reviewers noted, the bathrooms are small, but the outdoor showers are wonderful.
Charlottesville, US
Reviewed: Jul 24, 2016
Property Manager
Everything went very smoothly - thanks!
Pine Cliff is a great property - fantastic views, comfortable, and close to town.
Austin, US
Reviewed: Jun 19, 2016
Property Manager
Everyone we had contact with was pleasant and helpful.
The cottage was inviting and the view spectacular. The location is great - lovely, quiet setting yet close to all Boothbay Harbor has to offer. We appreciated the pleasant decor, the wi fi connection and the well equipped kitchen. The grounds and garden areas are inviting. Pine Cliff Cottage is well equipped and comfortable for a multi generational family get together.
North Conway, US
Reviewed: Sep 23, 2015
Property Manager
It was a great experience!! Everyone was helpful and kind and easy to work with. Great response time on emails and questions.
We loved the Pine Cliff compound!!! Being so close to the water and close to town was ideal. I really loved the stove in the kitchen- makes me want to buy a new one for my own house!!!
Chuluota, US
Reviewed: Aug 30, 2015
Property Manager
Stanley, US
Reviewed: Aug 10, 2015
Property Manager
Agency is problems here.
Location, dock, and deck are terrific. Kitchen is more than adequate. Bathrooms were much too small for us.
Lake Mary, US
Reviewed: Jul 4, 2015
Property Manager
The agency was helpful and very professional. Instructions were provided that answered any questions that we had. Great experience all around.
The property is beautifully situated overlooking the harbor. The views from the house are wonderful. The house is charming and very comfortable and spacious. The property had a great deck and outside eating area. Kraal so has a sundeck and water access to dock a boat. Great location near town and near restaurants.
Pratt, US
Reviewed: Jun 29, 2015
Property Manager
Everything went very smooth in arranging for this vacation through On the Water in Maine. There were no bumps in the road.
WOW is the word that comes to mind when describing the setting of this property. When you rent something online, it is always a gamble. With this one we hit the jackpot on setting!
Stony Point, US
Reviewed: Sep 17, 2014
Property Manager
On the Water in Maine is by FAR THE BEST rental agency we have ever worked with! We rent chalets, cottages or beach front homes every summer and/or fall, and this was our first time with On the Water in Maine. When you find someone on line, and are driving over 1000 miles to stay in a rental, you want to be sure you will have a "good" experience. Sometimes you are not sure what to expect when working with a new rental agency, but let me assure you, you will not find better communication or willingness to make your stay all you dreamed it would be than On The Water in Maine! The entire process from the on line reservation to check in and check out is streamlined and done with ease and fully explained through multiple emails, phone calls, and info when you get to your rental. If you take the few minutes to read the info they send you, you will know everything you need to know, and you will be assured you are working with a reliable rental agency! We would HIGHLY recommend On The Water in Maine as the BEST of the BEST when it comes to vacation rentals on the water in Maine!!! Not only will you have accurate photos of your rental (not deceptive ones like many would show), you will receive a list of equipment every rental will have so you know exactly how to pack! You will know how many towel sets, kitchen towels, soap dispensers.... everything! Just pack your food and clothes and you're ready to go! Honestly, I can't say enough good about our experience with On the Water in Maine!
We spent a delightful week at the Pine Cliff Cottage Compound in Southport ME. The cottage is absolutely charming and very comfortable and well equipped. The cottage is large enough to accommodate a large group, especially if the barn is also used, but the cottage was also very cozy for just my husband and I. There are 3 bedrooms, 2 of which have king sized beds, which I think is wonderful for a larger group or a couple of couples! The views are fabulous, and the master king sized bed was very comfortable, which is always important to me! The master, living room and kitchen all look right out on the water. There is also a screened in porch which we really enjoyed, and multiple decks and a dock. The kitchen is well equipped with far more tools than listed on the basic equipment list. The ONLY thing that might be a little less than desired are the frying pans. If you are health conscious and don't like to use scratched non-stick pans, you might want to bring your own frying pan, but all other pans and utensils were just fine. The Thermador stove was a treat to use, and the new heat system felt wonderful on those chilly evenings! I could not have asked for more than we found at the Pine Cliff Cottage Compound! Even my husband noted "it's going to be hard to top this one"! I couldn't agree more!!! - Comment from On the Water in Maine - Thanks for your great feedback! As you rented near the end of the season, it sounds like the non-stick frying pans are in need of replacing after a long, hard, summers' use. We will be doing exactly that for the 2015 season.
Reviewed: Aug 11, 2014
Property Manager
This is our 3rd year with On The Water In Maine. It is by far the best rental company we have every been with! The views from the property were amazing! The main house and guest house exceeded our expectations. The property is in a very private setting but we were still close to everything in the area.
Reviewed: Jul 28, 2014
Property Manager
I left almost half of my clothing for a three week vacation at a B&B in Pennsylvania on my way to Maine. They mailed my package to On the Water in Maine. The package had not arrived on Monday morning when I checked with them, but when I exited the Farnsworth Museum there was a message for me on my phone. The clothes I had been without for one week had arrived at the office, and they were on their way to deliver them. When I arrived at Juniper Bank my clothes were just inside the door. What a relief and what service from the team at On the Water.
Maxatawny, US
Reviewed: Jul 20, 2014
Property Manager
On the Water in Maine was great to work with, everyone I spoke with was very helpful and friendly.
Very quaint and cozy cottage and barn with absolutely beautiful views from the property. Very close to Boothbay and the shops and restaurants. Highly recommended and would definitely stay there again!
Wormleysburg, US
Reviewed: Jul 12, 2014
Property Manager
Everyone at On the Water in Maine was friendly and knowledgeable.
The property was well maintained and accommodated our family visit. The additional building, we called the "up house" (the barn), was perfect for providing extra space and sleeping for all involved. The Southport location was also perfect.
Reviewed: Nov 3, 2013
Property Manager
Highly enjoyable and very impressed with the house and the way everything was handled by On the Water in Maine.
Willow Streets, US
Reviewed: Sep 28, 2013
Property Manager
Justin at On the Water in Maine is terrific and most helpful.
New York, US
Reviewed: Sep 2, 2013
Property Manager
Every member at On the Water in Maine that we corresponded with was courteous and knowledgeable. A pleasure! Thanks especially to Emily :)
What a great spot! Truly a gem. We had a great time at Pine Cliff Cottage Compound - Fantastic view. House was really comfortable - from the kitchen to living room to bedrooms. Thank you so much.
Boxborough, US
Reviewed: Aug 27, 2013
Property Manager
Emily at On the Water in Maine was so sweet and very helpful. The outside shower at the main house is FANTASTIC! The lower deck with the chairs was a great place for coffee in the morning and cocktails in the afternoon. The house is very private despite having neighbors on both sides. The dock/view were really great. The floors needed to be better swept, and there were cobwebs around drapes and between furniture and the walls. "On the Water" was very receptive of our concerns about this though, and we appreciated that very much. They offered to have the cleaners come back (we declined) but they did give us a nice restaurant gift card (Thank you)! This house had everything we needed(except for kayaks) and we had a WONDERFUL TIME! We would definitely return to this location again. It would be a great place to have a large family gathering with the beautiful barn right across the street. We did not use the barn, but it looked lovely too.We also rented kayaks through Tidal Transit- and that was great too.
Thank you for allowing us to use your home. We had a wonderful time.
Michelle & Brian
Peru, US
Reviewed: Aug 17, 2013
Property Manager
Emily was very friendly and welcoming. Overall our stay was wonderful. The location was beautiful, watched an active osprey nest on the property and enjoyed seeing a bald eagle and a golden eagle. The kayaking was fantastic! The kids really enjoyed having the barn available.
New York, US
Reviewed: Aug 3, 2013
Property Manager
One hiccup which Justin, the owner of the rental agency handled personally, a prompt refund of cleaning fee was appreciated. Wonderful entertaining house, with screen in porch, several 'sun' decks and a lovely dock to tie up a boat or fish off of. As cooks we appreciated the Thermador oven and burner. Well stocked kitchen with pots, pans, bowls a kitchen larder which if thought about a utensil you found it. Very much appreciated. Very lovely communal spaces in both the house and the barn. Good air circulation and water pressure.
Thank you for making a family 60th party a welcomed one. Thank you for a welcoming home a great kitchen and making all us feel welcomed. Best to you and your family. Ken Merlo
Houston, US
Reviewed: Jul 21, 2013
Property Manager
Your employee Emily was a great support person. Always there, always cheerful and helpful. The view onto the water was great. When the sun started to come up at 4:08 AM it acted as our wakeup call to see a beautiful sunrise.
katonah , US
Reviewed: Jul 8, 2013
Property Manager


Smoking Is Not Permitted anywhere on or inside of any of our rental properties nor are those who may partake in tobacco smoking allowed to occupy any of our properties.

Occupancy may not exceed what is posted for each home. Maximum occupancy could include infants and children.

Amenities offered through On the Water in Maine Inc. are not available at all the properties we offer for rent. Boat Rentals through Maine Watercraft Rentals Inc. are offered Sunday morning to Friday after 4pm and include free delivery to the property. Check with an agent to find out what boats are available to rent at this property, or, when you process the booking here online, only the boats available for the property will be listed as available to rent.

Please see our Rental Guidelines Page for further questions regarding how to book this property and additional charges and fees. Contact a reservation agent for more details or to ensure you are booking the right property for you.

Town Info - Boothbay, Boothbay Harbor & Southport Island

Boothbay Harbor is one of the best-known boating centers in New England and boasts a natural harbor known as "The Boating Capital of New England," home to many fishing boats as well as pleasure craft. Southport Island borders the south side of Boothbay Harbor and is accessible by a bridge.

Learn More