Entire home

Classic Island Cottage

Photo gallery for Classic Island Cottage

A sailboat with multiple sails docked at a marina with several smaller boats and a pier.
A rustic kitchen with a wooden table, chairs, a stove, and a brick wall with a clock.
A two-story house with a front porch, a blue door, and a bicycle parked outside.
A white porch with a white railing, a bench, and a chair. There are steps leading up to the porch, and a small garden area with flowers.
A sunlit room with a beige sofa, patterned pillows, and wooden chairs.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Casco Bay

Popular amenities

  • Patio
  • Barbecue grill
  • Refrigerator
  • Washing machine
  • Internet
  • Onsite parking available

Explore the area

View in a map
Peaks Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Umbrella Cover Museum
    ‪7 min walk‬
  • Place, Fifth Maine Museum
    ‪8 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪41 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

Add dates for prices

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About the area

Peaks Island

Located in Peaks Island, this cottage is in the city centre and on the waterfront. State Theatre and Thompson's Point are cultural highlights, and travellers looking to shop may want to visit Maine Mall. Maine Sports Hall of Fame and Maine Narrow Gauge Railroad are also worth visiting. Sailing and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and mountain biking nearby.
View more Cottages in Peaks IslandOpens in a new window
Map
Peaks Island, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Richard Boyd Art Gallery - 5 min walk - 0.5 km
  • Umbrella Cover Museum - 7 min walk - 0.6 km
  • Fifth Maine Museum - 8 min walk - 0.7 km
  • Battery Steele - 16 min walk - 1.4 km

Getting around

  • Portland Transportation Center - 40 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 48 min drive

Restaurants

  • ‪Brickyard Hollow Brewing Company - ‬27 min drive
  • ‪Twelve - ‬28 min drive
  • ‪Second Rodeo Coffee - ‬33 min drive
  • ‪Saltwater Grille - ‬33 min drive
  • ‪Duoro - ‬28 min drive

Frequently asked questions

Is Classic Island Cottage pet-friendly?

No, pets are not allowed at this property.

How much is parking at Classic Island Cottage?

On-site parking is available at the property.

What time is check-in at Classic Island Cottage?

Check-in begins at 3:00 PM.

What time is check-out at Classic Island Cottage?

Checkout is at 10:30 AM.

Where is Classic Island Cottage located?

Located in the heart of Peaks Island, this cottage is within a 10-minute walk of Casco Bay and Umbrella Cover Museum. Fifth Maine Museum and House Island are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 102 out of 116 reviews
Rating 8 - Good. 12 out of 116 reviews
Rating 6 - Okay. 2 out of 116 reviews
Rating 4 - Poor. 0 out of 116 reviews
Rating 2 - Terrible. 0 out of 116 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hosts instructions for directions and property info was very helpful
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a fantastic cottage that we enjoy returning to each year.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely cottage. Plenty of room and very comfortable. Host was responsive with communication. We would definitely book again.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This roomy cottage is charming and conveniently located within walking distance of everything you’d want to do on Peaks Island. Checkin and checkout were smooth, and the host was gracious and quick to answer questions. What a fantastic trip!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, listing accuracy
Disliked: Communication
The cottage was very clean, with comfortabe furniture and lovely back deck and side porch
Stayed 14 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quaint cottage on a lovely island near Portland. Responsive and thoughtful owners. Convenient access to the ferry, beaches and ice cream. Great place to retreat for a few days. Lots of outdoor seating, friendly people and even a neighborhood cat! Comfortable beds and clean and well-equipped kitchen. Enjoy!
Stayed 6 nights in Sep 2026
Response from VrboOwner on 21 Sept 2026
Thanks so much! So glad you enjoyed your stay! Welcome back anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean and simple, such an amazing stay on Peaks!
Stayed 3 nights in Jun 2026
Response from VrboOwner on 14 Jun 2026
Welcome back any time! Thanks for being great guests.
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
We absolutely loved our stay here! The house was super spacious and in a perfect location. Will definitely be back!
Stayed 2 nights in May 2026
Response from VrboOwner on 18 May 2026
So glad you had a great stay! Thanks for being great guests. Welcome back, anytime!
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication
Disliked: Location, listing accuracy
N/A
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Stayed 2 nights in Sep 2025
Verified review

6/10 Okay

Liked: Cleanliness, communication, location
The linen rental was a late complication resulting in buying & bringing our own. The departure deadline was tough to complete washing & drying easily. No recycle bin inside, & still requirements for handling safe trash handling for the island (no purple bags provided). More lights would be helpful upstairs; glad I had my headlight.
Stayed 3 nights in Sep 2026
Response from VrboOwner on 19 Sept 2026
Sorry your stay wasn't more enjoyable for you. Guests are clearly notified about sheets in the listing and at the time of booking, and details are provided for arrangements ahead of time. Recycle bin is outside and easily accessible. Purple bags are a problem on the whole island now, but this could have been explained if the guest had reached out about it. We will check bulbs for any necessary replacements, but have never received complaints about lighting.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tim was great to deal with. He made an emergency call to peaks island fuel company, and quickly resolved an issue at the start of Memorial Day weekend. We had a great time
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We so enjoyed our visit to Peaks Island. It’s was a dream! The house was absolutely charming. Kitchen was well stocked. Timothy was very responsive with questions and very helpful with any questions we had. Just a couple of things to know for potential renters: Bedrooms are located on second floor. This was not a problem for us , but for someone who may find it difficult to climb a moderately steep staircase, this may be a concern. Also, know that sheets are not provided. Renters must bring sheets, make their beds, and take them off before leaving. Lastly, housekeeping requires the renter to take all garbage to the transfer station themselves before leaving. The transfer station is approximately 1 mile away. So, renters who do not bring their personal vehicle for their visit to the island are forced to either rent a cab or a golf cart to deposit their garbage prior to leaving. Otherwise, the house and the island were a dream. The house was the perfect place for a girls trip for my mom’s 70th birthday celebration.
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, and good location. Thanks! We had a very pleasant experience
Stayed 2 nights in Oct 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

Great cottage on peaks!
Stayed 2 nights in Oct 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tim was a wonderful host! Very helpful and checked in several times. The house is larger than it appears in the photos online! Location is great. We’d definitely stay here again!
Stayed 7 nights in Aug 2025
Response from VrboOwner on 19 Aug 2025
So glad you had a great stay. We’d love to have you back any time!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming house on charming island

Lovely very well maintained house very close to “Downtown” Peak’s Island.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely incredible! We couldn’t have asked for a more perfect vacation home, location or experience. Tim was so easy to communicate with and made sure that everything was in order for our stay. Definitely will be coming back!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A wonderful summer house on Peaks island.

We thought it was perfect.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent experience!
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just lovely

Great location (quiet but close to everything). Very comfortable and relaxing spot with an excellent porch, there is even a peek of blue from the rocking chair. Hosts were super communicative and helpful!
Stayed 7 nights in Jun 2025
Response from VrboOwner on 21 Jul 2025
Glad you had a great stay. Thanks for being great guests!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

We had a wonderful time. The cottage was very well equipped.

The cottage was very comfortable. The owner was very helpful with answering questions.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 9 Oct 2022
We are so glad your stay was good! Come back any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

We stayed in this cute charming cottage for our anniversary. Close to the restaurants and ferry. Enjoyed our stay! Would recommend!
Stayed 3 nights in May 2024
Response from VrboOwner on 26 May 2024
Thanks, Mary! Thanks for being in such close touch during your stay. It was great having you---come back any time and--happy anniversary!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Long Weekend Getaway

Absolutely lovely home with amazing history and character! Super convenient spot on the island with plenty to do! We really enjoyed our time here and hopefully we will be back! Great hosts as well.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 22 Apr 2024
Thank you, Sydney! Please come back any time!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint Getaway

We enjoyed the peaceful and friendly neighborhood. It was a close walk from the ferry.
Stayed 2 nights in May 2023
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