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Book Online or call HomeAway Booking Assistance 888-640-7927

Oceanside Tower Ultimate Comfort/ Lighthouse View

Bedrooms 3
Half Baths1
Space 1,800 sq. ft.
Property type house
Minimum Stay 1 - 7 nights


About the property

2 bedrooms, 1large loft room ,1.5 baths

Exciting ocean views spectacular sunrises and sunsets from the many windows of this three-story home located on Bailey Island's highest point of land. Your fully appointed gourmet kitchen is equipped to cook meals for up to 15 people. A dining area, breakfast-nook, sun room, powder room, living room complete the first floor. Wide pine plank floors continue onto the second floor, where you will find a library area, two bedrooms, large full bath, and sun deck.

Third floor sky room loft features a lighthouse perspective of the Atlantic Ocean to the east, Mackeral Cove, Merriconeag Sound, and the Presidential Mountain Range to the west --an essential part of your every sunset party. An antique claw foot tub, futons to sleep six, a writing desk, an entertainment center, and a collection of antique sleds complete the sky room. A paddle fan suspended from the open rafters promotes breezes for a comfortable environment.

LOCAL attractions include the one- of- a -kind Cribstone Bridge, the Giants Stairs, Kayak lessons and tours, boat tours and rentals, bean hole suppers, lobster bakes, local auctions,craft fairs, and art shows, Eagle Island tours ( Admiral Peary's summer home), 'Island Romance' boat tours of surrounding islands,and the annual lobster boat races.

NEARBY attractions include LLBean, Maine State Music Theater, outlet shopping in Freeport, golf, sailing, hiking.

Also nearby is Portland and its many offerings in arts, dining, entertainment, historic lighthouse tours, and BEAUTIFUL beaches just south of the city! Less than an hour to the north is Boothbay Harbor with much of the same PLUS the beautiful botanic garden recently opened there, a narrow guage railway museum in the 'prettiest village in Maine', antiquing, local farmers markets, and agricultural fairs and midways.

Something for everyone!

For those of you who want to stay put and RELAX, this is the best place in the world to do just that!

More Details


Bailey Island House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1800 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 10
  • Max. adults: 10
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only
Location Type:
  • Beach
  • Near The Ocean
  • Ocean View ...
  • Water View
  • Away From It All
  • Budget
  • Family
  • Historic
  • Tourist Attractions
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer
  • Filtered Water
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking
  • Sofa Bed
  • Telescope
  • Toilet Paper
  • Towels Provided
  • Water Cooler
  • Wireless Internet
  • Wood Stove
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Lobster Pot
  • Microwave
  • Oven ...
  • Pantry Items
  • Refrigerator
  • Stove ...
  • Toaster ...
  • Child's Highchair
  • Dining
  • Dining Area
  • seating for 12 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom - toilet , sink
    Bathroom - toilet , shower , sink
  • A claw foot bathtub is located on the top floor. Suitable for bathing children, or for a relaxing soak in the tub - with a birds eye view of Casco Bay to the south, sunrise and the Atlantic Ocean to the east, Merriconeag Sound and the White Mountains of New Hampshire/sunset to the west!
  • 3 Bedrooms, Sleeps 10
  • Bedroom - 1 queen
    Bedroom - 1 double
    Bedroom - 3 sleep sofa /futon
  • The top floor loft space serves as a third bedroom and has 3 double size futons. The sleep sofas in living room and first floor private sunporch room, offer additional sleep options
  • Books
  • Books for Adults
  • Books for Kids
  • DVD Player
  • Games
  • Games for Kids
  • Radio
  • Satellite / Cable
  • Television
  • VCR
  • Balcony
  • Beach Chairs
  • Beach Towels
  • Bicycles ...
  • Binoculars
  • Deck / Patio
  • Golf ...
  • Kayak / Canoe ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Small Cooler
  • Tennis ...
  • Walkway to Water
  • Wood Deck
  • 2 bicycles
  • 3 garden chairs
  • 5 beach chairs
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • autumn foliage
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • forests
  • library
  • live theater
  • marina
  • museums
  • pond
  • recreation center
  • restaurants
  • synagogues
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • pier fishing
  • sailing
  • swimming
  • tennis
1 queen, 1 double, 3 double futons on top floor loft. Internet, tv on each floor, PO box. lobster cooker, gas grill . hammock, picnic table, bikes, large parking lot, RV power H.U., rock garden/cutting garden


Exceptional! 5/5 -
(7 traveler reviews)

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Oceanside Tower Ultimate Comfort/ Lighthouse View
average rating of 5.0 based on 7 reviews

Absolutely recommended!

  • 5 of 5

We had a wonderful time staying at this place and regretted deeply that it was for only 2 nights. The house has everything you might possibly need, from a fully equipped kitchen, an amazing top floor room with beautiful view to lots of comfy sitting nooks. It is spacious and nicely decorated and the location on Bailey Island couldn't be any better, within walking distance from everything. Wi-Fi was strong. Sherri is a most considerate host and we are already looking forward to staying again in this place! (October, 2017)

  • Submitted: Oct 13, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Oceanside Tower

  • 5 of 5

This location was a great place to stay. Everything we needed for making our meals was at hand. Don't let me forget to mention that there is availability of a steamer for lobsters - which we took full advantage of. The top floor view is amazing. Sherri was always available to us if we needed any assistance with anything. Bailey's Island was a fun place to stay. Many places to go on your morning walks... and if you catch an evening sunset, they are beautiful. Just a short ride from the famous cribstone bridge, also. Lands End is just a ways down the street.

  • Submitted: Jul 18, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Beautiful Home!

  • 5 of 5

I rented this property for my bridal party to stay at the week of my wedding and everybody had a fantastic time and loved the house. I have never rented a property where the owner was as sweet and kind as Sherri. She made everything related to the house stress free during an extremely stressful week. I would definitely rent this place again if I vacation in the area in the future.

  • Submitted: Jun 21, 2017
  • Stayed: May 2017
  • Source: HomeAway
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Already planning our return!

  • 5 of 5

Our family of 5 LOVED this home. Sherri has paid so much attention to detail and ensures that her guests are extremely comfortable. We were arriving late and she turned on the heat so my kids would not be chilly. As we pulled up, the top floor was illuminated giving the house a "lighthouse" look and we knew we were at the right destination. The kids slept on the top floor and enjoyed the 360 views at sunrise to gently wake them. The antiques, collectables, repurposed items....all of it made this home so charming. Kitchen and linen closets are well supplied, we didn't need to bring anything but whatever we wanted to cook and toiletries, which was great with an already full mini van lol.

We cannot wait to come back and are already looking at our calendar.

Sherri, thank you, thank you for helping to make my 40th birthday weekend a great one for my family! ps- Cooks was delish!

  • Submitted: Oct 17, 2016
  • Stayed: October 2016
  • Source: HomeAway
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3 0

Fun, fun place!

  • 5 of 5

We had such a wonderful time here! Sherri has the house decorated so uniquely with all kinds of treasures. The house has everything you need! Loved visiting all the beautiful places on the island and made a trip up to Acadia National Park. The lobsters were out of this world and my grandkids loved seeing the touch tank. Everyone was so friendly on the island. We will certainly make this a place to come back to.

  • Submitted: Aug 13, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
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3 0

A spectacular gem surrounded by shimmering waters.

  • 5 of 5

Beautiful home with gorgeous views from tower. Ocean views from all windows on third floor. Home owner is incredibly nice. The island itself is full of history and wonderful restaurants. The BIGs store seem to serve the biggest, sweetest blueberry pancakes on earth. On the first night we ate at the church and had homemade chowder and desserts and we felt like true islanders. Additionally, the islanders are friendly and open. If you are like for a break from the day-to-day grind, and are seeking beautiful sights and history, this is the place for you.

  • Submitted: Jul 22, 2015
  • Stayed: July 2015
  • Source: HomeAway
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Property Manager

Sherri Duprey
Member since: 2010
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
February 13, 2018


Nearest Airport
36 Miles
Portland International Airport
Nearest Barpub
1 Miles
Cooks Restaurant
Nearest Golf
14 Miles
Nearest Train
14 Miles
Brunswick - Amtrak
Nearest Motorway
14 Miles
Brunswick Maine
Nearest Restaurant
0.1 Miles
Giants Stairs-
Nearest Beach
1 Miles
Cedar Beach
Car: recommended

Bailey Island is a quiet lobstering community that delights visitors summering on the Maine coast. Sandy or rocky beaches, easy access to waterside hiking, kayaking, and bicycling make this half mile by two mile island a special place. Three restaurants, churches, boat charters (sail, touring, fishing), and a general store make life here 'island easy.' Everything to do on Bailey Island is only a short walk away.


For those who love to shop, the towns of Brunswick and Freeport offer major name brand outlet stores for bargain hunters, as well as malls and discount stores that are all within a few minutes drive to the mainland. The scenic and historical communities of Bath, Boothbay Harbor, Portland and Wiscassett are all within an hour drive; in addition, golf courses, movie theaters, performance theater, art galleries and museums, live music, cultural festivals, horseback riding and restaurants are also short distance away.




Additional information about rental rates

Refundable damage deposit $200
Tax Rate 9.0%

During the off season, a three (3) night minimum is requested. Price is pro rated based on the weekly off season rate.

50% deposit
balance due at check in

Manager's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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