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Hilltop Cottages Overlooking Penobscot Bay, Stonington Village

Bedrooms 2
Space 900 sq. ft.
Property type cottage


About the property

Rented by wk. or mo.Cottage, 2 Bedrooms + futon, 1 Bath, Sleeps 4-5

Two cottages overlooking Penobscot Bay and Stonington Village rented as one unit at the end of a dead end street at the edge of a forest. Private, quiet, yet two minutes walk to Village, public dock, and boat ramp.

South cottage has well equipped Kitchen, Dining area, Living room with fold out futon, and woodstove. Spiral stair leads to large Bedroom with queen bed. North cottage, a few feet away, has the bathroom, a large sitting area suitable for children's play or studio, new washer and dryer. Upstairs has bedroom with two single beds. The backyard has a large lawn with adirondack chairs and table.

Both Cottages are light and airy and catch the Sea breeze.

Keywords: 2 Cottages rented as 1 Unit

More Details

Lorraine and Ben Jeffries
Member since: 2004
Speaks: english, finnish, Beginner Finnish
Response time:
Within a few days
Response rate:
Calendar last updated:
July 21, 2017

About Lorraine and Ben Jeffries

I am a retired restauranteur who as a youngster sailed with my grandfather from Massachusetts to Maine many times. When I sold my restaurant, my wife and I headed back to a more simple life. We use woodstoves to heat our house, my wife's studio and the cottages. Until quite recently, I split and stacked all the wood. I read a lot and quite a collection of books. My wife has her studio nearby and she likes to paint winter scenes and in other seasons. In the Fall, we take our dog bird hunting for partridge and woodcock. My wife's a crack shot, so I have to mind my P's and Q's. Mostly, I like to sit on our deck in the sun and look out at the harbor view. In winter we may get the occasional power failure, so we trot the candles and of course we have the woodstove going.

Why Lorraine and Ben Jeffries chose Stonington

We bought the property from a retiring schoolteacher mostly to save it from being torn down and rebuilt as a modern structure. My artist wife had done paintings of it in winter and we were charmed by the unique detailing of the cottages. We wanted to keep that "Stonington flavor" for as long as possible. My wife painted the interior in bright colors a la the Swedish painter Carl Larsson.

What makes this cottage unique

You may enjoy seeing the wildlife. Deer, fox, rabbits,partridge, coyotes occasionally come around and watching the red cardinals feeding on the beach plums. In summer, the huge schooners sailing by or into the harbor is an extraordinary sight. Being able to walk places in town is a big the post office, the restaurants, bank, town office and opera house. The boat ramp is close by. The Granite Museum is a great place to learn about the history of this quarrying town. Hiking is a good way to explore the area.


Stonington Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 900 sq. ft.
House Rules:
  • Max. occupancy: 5
  • pets considered ...
  • children welcome ...
  • non smoking only ...
Location Type:
  • Downtown ...
  • Monument View ...
  • Mountain View ...
  • Ocean View ...
  • Village ...
  • Water View
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Broadband Access ...
  • Clothes Dryer ...
  • Free Long Distance
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Parking Off Street
  • Parking for RV/Boat/Trailer ...
  • Telephone
  • Towels Provided
  • Washing Machine ...
  • Wireless Internet
  • Wood Stove ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom 1 -
  • 2 Bedrooms, Sleeps 5
  • Queen size Beds (1), Twin or Single Beds (1), Sleep Sofa or Futons (1)
  • Games ...
  • Deck / Patio
  • Lawn / Garden ...
  • Outdoor Grill
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • churches
  • cinemas
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • gambling casinos
  • photography
  • scenic drives
  • shelling
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • hunting
  • kayaking
  • pier fishing
  • rock climbing
  • sailing
  • swimming
  • tennis
  • wind-surfing
Full Kitchen with Extensive Pots, Pans & Bakeware, Excellent Knives, Utensils & China, Cooking


4.3/5 -
(3 traveler reviews)

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Hilltop Cottages Overlooking Penobscot Bay, Stonington Village
average rating of 4.3333335 based on 3 reviews
Somerville, MA

First family vacation a success!

  • 4 of 5

My husband was working on a production at Stonington Opera House and we decided to make a vacation out of it. We = Husband, me, 11 month old child and water loving labrador. The cottages were PERFECT. The great big backyard allowed enough space for the baby to play and the dog to run. The location made it possible for all of us to walk my husband to work each morning through the town center. The cottages are well equipped for cooking and cozy for reading. We had friends join us for two nights and with two cottages there was plenty of space for us all.

Lorraine was such a great host: even having a special rocking horse for our baby to play with. She and Ben are just two houses away and readily available to help should we have needed it (we didn't really).

I'd give it 5 stars except for the spiral staircases up to the sleeping areas which were a little tricky to manuever while carrying a little one and our dog couldn't make it up the stars. But honestly it was that big a deal.

A big thing that i loved: excellent wifi so I could stay connected but no TV so i couldn't veg out.

  • Submitted: Aug 30, 2017
  • Stayed: August 2017
  • Source: HomeAway
Owner's Response: We're glad you enjoyed your visit !!
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Beautiful Anniversary Trip

  • 5 of 5

From the first contact with the owners, I knew we had chosen the right place to spend our anniversary in Maine. They were extremely kind, helpful and welcoming. My husband, our yellow lab and our brother and sister-in-law spent a week at Hilltop Cottages. The Cottages were very clean and contained everything we needed. They were reminiscent of earlier, simple times, which was relaxing. It was a terrific set up to have two separate cottages to stay in allowing for privacy and space while travelling with others. The setting is lovely with a private backyard that our dog loved. Close to town and walking to restaurants, gift shops and fishing pier. Close to beautiful beaches. A very magical place and we will treasure the memory for years to come.

  • Submitted: Sep 26, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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May 2014

  • 4 of 5

We stayed at this quiet, peaceful location in May 2014. I'm writing a review now because we find ourselves still (almost two years later) talking about it and sharing the stories and photos with our family and friends. We selected this location so that we could bring our black lab on vacation with us. It was perfect for him to exercise in the backyard, and is located on a cul-de-sac with only two other cottages. We walked him into town to enjoy the scenic Maine seaside village. Our son met us here after a short drive from Maine Maritime Academy, and enjoyed a few days with us too. The guest homes are rustic, and comfortable. We stayed in the larger home, and our young adult son appreciated having his own accommodations in the smaller cabin. The architecture is historic, and makes you appreciate the simpler times. The property has a feel that can only be naturally created, and is nestled on an elevation that provides you with a spectacular view of the water and arriving sailboats and fishing vessels. The Owners were very kind, accommodating, and extremely responsive. It was important to them that we had a comfortable stay, and they checked in with us to confirm. It was very easy to relax and enjoy our time here together as a family, and leave the complicated, hectic work week behind. Thank you Hilltop Cottages for your hospitality!

  • Submitted: Mar 28, 2016
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
Owner's Response: what a lovely and thoughtful review !! Thank you !! Meeting the people makes the rental business all worthwhile. I have thought about you people as well. I think your son might be interested in reading "Voyage Around the World" by Sir Joshua Slocum. Safe travels !! -Lorraine
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Nearest Airport
45 Miles
Bangor International
Nearest Barpub
0.1 Miles
Fisherman's Friend
Nearest Ferry
0.1 Miles
Isle au Haut Ferry Services
Nearest Golf
5 Miles
Island Country Club
Nearest Motorway
44 Miles
I-95 Brewer Maine
Nearest Beach
1 Miles
Sand Beach

Deer Isle and Stonington is a lovely island connected to the mainland by a green suspension bridge. Our island is an outdoorsmens dream. Kayaking, sailing, biking, boating, hiking and sightseeing are just some of the great things to do on our small and amazing island.


Rates & Availability

Taxes and fees are additional
This calendar has not been updated in over 2 months and the availability shown may not be accurate.

Additional information about rental rates

Tax Rate 9.0%

We try to maintain weekly rentals from Saturday to Saturday. arrival after 4 pm and leaving by 10 am. some exceptions may be made for shorter stays in the off season.

refundable $200 security deposit due to save dates, rest due 2 weeks before arrival

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

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