Peaks Island: Spectacular Oceanside Retreat

Oceanside Retreat
“ Excellent ”
3 Reviews
68 Winding Way, Peaks Island, ME 04108


Bedrooms: 3
Bathrooms: 2.5
Sleeps: 8
Type: Home
Per week: $3,500
Pets allowed: Yes
Internet: Yes
Description of the Peaks Island vacation home rental
Spectacular Oceanside location. Breathtaking views of ocean, light houses, nearby islands, ships and open ocean. This beautiful three level, 3 bed room, 2.5 bath Victorian Shingled Style home has all you’ll need for a wonderful and memorable vacation.

1st level has 2 guest/family bedrooms, bath, laundry, family room,w a daybed & covered porch.

2nd level has open living, dining & a well appointed kitchen and a deck with all the ocean views you can imagine. The back has a covered porch for grilling.

3rd level is the master suite. Custom bathroom w/ double sinks, soaking tub, shower & laundry. There’s a turret sitting room with views in every direction! From the king size bed you can lay and watch the moon glimmer on the ocean and the sound of surf will lull you to sleep.

The setting is equally as spectacular as the house. Incredible ocean views all in front & in back, it looks out over a freshwater pond, nature trails & natural seaside vegetation. There’s a spacious lawn for playing and gathering and the property is but a 15 min walk to the ferry & village or 5 min. bike ride. Surely one of the finest properties on the Island.

At $3,600.00 per week, you won’t be disappointed.
Area Information
Peaks Island offers the best of both worlds; a small, safe, beautiful and peaceful place at the doorstep of one of the nicest small cities in the country. Peaks is the second largest island in Casco Bay and one of the most picturesque places of natural beauty of all the east coast. Peaks village area, "Down Front" has 4 restaurants, an ice cream/candy store, a large food market w/ video rentals, gift shop, public library, health center, a pub, bike & kayak rentals, art gallery, museum, horse riding camp, beaches and a Sailing and tennis club.

Peaks is a 15-20 min. ferry ride from the city of Portland. The ferry schedule runs nearly on the hour till 11:30 pm at night in summer. Portland ranks as one of the top small cities in the US offering a full array of entertainment, dining, shopping and all within easy walking distance of the ferry terminal. Portland is just a two hour drive to downtown Boston and twenty min. ride to Freeport, home of LL Bean and other great shopping. Portland offers public transportation and an international airport.

Availability Calendar


Begins Ends Week
Weekly Monthly Min
Jan 01 2015 Dec 31 2015 - - $3,500 - 6 Nights
Check In: 12 p.m. Check Out: 11 a.m.
Lodging tax: 8%
Deposits: We require 2 separate checks; 1 for rent and lodging tax and 1 for security deposit
Payment Options: Cashier's Check, Personal Check
Other Fees: A non-refundable pet deposit of $100.00 per pet is required. Linens, cleaning and trash removal services are available for fee; contact owner for details. Golf cart rentals also available on island.


  • Beds

  • 1 King Bed
  • 4 Twin Beds
  • 1 Sofa Bed
  • 1 Crib
  • 1 Queen Bed
  • Features

  • Balcony
  • Heating
  • Pet Friendly
  • View (Water)
  • Beach Chairs
  • High Speed Internet
  • Porch
  • Wood Stove
  • Full Kitchen
  • Parking Included
  • View (Ocean)
  • Appliances

  • Alarm Clock
  • DVD Player
  • Microwave
  • Stove
  • Blender
  • Dishwasher
  • Oven
  • TV (Cable/Satellite)
  • CD Player
  • Gas Grill
  • Radio
  • Toaster
  • Ceiling Fan
  • Hair Dryer
  • Refrigerator (Full)
  • Washer/Dryer
  • Coffee Maker
  • Iron
  • Stereo
  • Activities

  • Bicycling
  • Park
    (<1 mile)
  • Boating
    (3 miles)
  • Windsurfing
    (4 miles)
  • Hiking
  • Playground
    (<1 mile)
  • Deep Sea Fishing
    (3 miles)
  • Golf
    (5 miles)
  • Ocean
  • Restaurant
    (<1 mile)
  • Gym/Fitness Center
    (3 miles)
  • Racquetball
    (5 miles)
  • Basketball Court
    (<1 mile)
  • Shopping Area
    (<1 mile)
  • Movie Theater
    (3 miles)
  • Miniature Golf
    (7 miles)
  • Beach
    (<1 mile)
  • Snorkeling
    (<1 mile)
  • Whale Watching
    (3 miles)
  • Surfing
    (8 miles)
  • Fishing
    (<1 mile)
  • Horseback Riding
    (1 mile)
  • Bowling
    (4 miles)
  • Amusement Park
    (10 miles)
  • Grocery Store
    (<1 mile)
  • Sailing
    (1 mile)
  • Pool
    (4 miles)
  • Winery
    (25 miles)
  • Kayaking
    (<1 mile)
  • Tennis
    (1 mile)
  • Scuba Diving
    (4 miles)
  • Zoo
    (25 miles)
  • Live Entertainment
    (<1 mile)

Other Vacation Rental Amenities
Portland's offerings include: a Children's Museum, skateboard park, great restaurants, several art museums, movie theater, whale watching, excursion boats, fishing guides, live music, theater, farmers market and Windjammer rides all within walking distance of the ferry terminal

Reviews for this vacation home rental in Peaks Island, Maine

Have you been a guest of this property? Write a review!
Sue McCarthy

Sue McCarthy

Woburn MA

loved it

March 3, 2015

What a terrific week. Besides being blessed with great weather the house exceeded our expectations with the pond view from one side and outstanding ocean views from the front. The house offered us all the amenities one could want - great kitchen and bath, views, deck and a lovely yard. We stayed with our two teenage children whom enjoyed exploring the island on their own, it is very safe and offers a lot with the beaches, Battery Steel and quaint downtown. The owners were friendly, and very accomodating and offered many suggestions of what to do on and off the island. We hope to have the chance to stay again at this property.

Laurie Borek

Laurie Borek


Renters Beware

September 28, 2011

The home and views are incredible. However, the owners shouldn't be renting their property. They are very strict , we arrived during "Irene". The property owner was complaining how the previous occupants were slobs. He spent the beginning of our stay mowing the lawn and running around the property during the storm. We left the home cleaner than we arrived except for 2 red wine spots on the white slip covers on the sofa's and were subject to a replacement fee. When they said we could dispute this and we did, they never responded back and kept $30.00 from a $1500 security deposit. "All in all" we had a wonderful vacation despite the property owners and their frugal hospitality.

Ralph and Jeannie Ashmore

Owner's reply:

We had no control over "Irene" and as for your running around the property, that's your issue!! We have a lawn service, not sure why you mowed??? WoW $30 for a permanent stain? Break the bank!!
It's a waterfront home! We are protective of it. Wouldn't you be? Sounds as if you had a great vacation and enjoyed the incredible home and views. Could it be that bad? Guess you were safe during "Irene" but did you forget that?
Thanks so much for staying with us...

bill bunting

bill bunting


weird owner

February 17, 2009

we reserved this house for a family trip. It was advertised as the finest house on Peaks Island, yet it was a duplex with tenants living below our house. In the rear of the unit was a "yurt" that the owner also either rented out or used for his own purposes. It was like staying in a compound. The owner is very strange and demanded access to our unit on more than one occasion.

Ralph and Jeannie Ashmore

Owner's reply:

We've ironed out many issues since we started renting. The yurt is now a 4th and very private bedroom for one. It has a pond view too and is very cozy and adventurous!!!
We only rent the house to one family at a time. Come on...
No we don't need nor do we "demand access" to the house.
We are good people and as homeowners we want our guests to enjoy and treat our home with the same respect that we would treat yours.
Jean and Ralph Ashmore 2013 owners..

Owner Supplied Testimonials

The house is a 3 level building, built in a wonderful private location. It has lawn in the front and back for the family to enjoy running around with the dog and kids. Coffee on the back porch is a treat in the AM. I highly recommend it. A little sun on the open deck is also great place to watch the waves, boats, people or just read in peace and quiet. It's a comfortable house, not ostentacious and has what you'll need. If not we'll get it for you. We want your stay to say, "we'll be back!"

Frequently Asked Questions

Q: Why would I want to stay here?
A: CHILL_AX!!! Walk the beaches, find sea glass and shells, kayak, visit in Portland, ME. It's such a private location compared to some other island properties.
Q: What makes our house special?
A: Our home is comfortable, lived in, easy to relax in. The location is fabulous, and you can see 2 lighthouses from the front of the house. Hear and see the ocean, go birdwatching in the back pond, walk in the woods...
Q: What so fun to do on the island?
A: Kayak to Fort Gorges, eat lobstahs, walk around the island.. fall asleep to the waves...zzzzzzzzzz, scope out the history of the island, explore Battery Steele, visit the Civil War Museum, 5th Maine and the 8th Maine, take at one of our 3.5 restaurants, sit on the rocks, explore tidal pools, do nothing but read

Interested in Renting this Property?

Page Views This month: 93 This year: 254 Since listed: 10,074
Last updated: March 3, 2015

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Owner Profile

Ralph and Jeannie Ashmore

Ralph and Jeannie Ashmore


More about the owner
  • School:

    The Brick School. k-5
  • About:

    We both have lived on the island for years. My husband is 4th generation coming to the island during the summers from MA. I have lived on the island for 18 years now. We were married on the island at the 5th Maine Museum on a sunny warm, windy day in August, 17 years ago. My husband's son, Nate, ...
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