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Classic Island Cottage

Photo gallery for Classic Island Cottage

Close to Portland
Exterior detail
Large, open Kitchen and dining area.
The Magpies Nest
Sun porch, afternoon sun.

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 Fifth Maine Museum
Sleeps 6•3 bedrooms•3 beds

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Barbecue grill
  • Deck or patio
  • Internet access

Explore the area

View in a map
Peaks Island, ME
  • Place, Richard Boyd Art Gallery
    ‪5 min walk‬
  • Place, Umbrella Cover Museum
    ‪7 min walk‬
  • Place, Fifth Maine Museum
    ‪8 min walk‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪40 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

About this property

Classic Island Cottage

Spacious, charming 1896 cottage at the top of quiet, magical footpath. Has a secluded, peaceful feel but is only a 2-3 min. walk to island grocery store, restaurants, coffee shop, ice cream, 5 min. to ferry and 8 min. walk to Sandy Beach. Also convenient for weddings at the Inn. Relax on the sun or open-air porches, read a book by the gas fireplace at night, grill your dinner on the back deck or pop in to Portland for a day trip on the ferry. The cottage retains a rustic feel, but various updates (e.g., comfortable beds) make this a delightful home-away-from-home for your relaxed island holiday. (Please note that guests bring their own sheets, but we provide blankets, pillows. duvets and bath towels) Welcome to the Coast of Maine! STHR-000215-2018

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House Rules

Check in after 3:00 PM
Check out before 10:30 AM
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Children

Children allowed: ages 0–17
Children welcome
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Events

No events allowed
Please ask for more than 3-4 guests.
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Pets

No pets allowed
Pets not allowed
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Smoking

Smoking is not permitted
Non smoking only
Guests must be in touch with Tim via phone, the owner, within one week of booking, if booking is two or more weeks in advance. 2 days if 2 to 1 week

Important information

You need to know

Property # 3687176
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: Please ask for more than 3-4 guests.
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Peaks Island

Located in Peaks Island, this cottage is in the city centre and on the waterfront. State Theatre and Portland Head Light are notable landmarks, and the area's natural beauty can be seen at Thompson's Point and Higgins Beach. Maine Narrow Gauge Railroad and Portland Observatory 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 cycling and mountain biking nearby.
View more Cottages in Peaks IslandOpens in a new window
Map
Peaks Island, ME

What's nearby

  • 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
  • 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

  • ‪Second Rodeo Coffee - ‬33 min drive
  • ‪North43Bistro - ‬33 min drive
  • ‪Twelve - ‬28 min drive
  • ‪Cumberland Farms - ‬32 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 does it cost to stay at Classic Island Cottage?

As of 29 Jul, 2026, prices found for a 1-night stay for 2 adults at Classic Island Cottage on 27 Sept, 2026 start from S$876, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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, Richard Boyd Art Gallery 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. 96 out of 107 reviews
Rating 8 - Good. 11 out of 107 reviews
Rating 6 - Okay. 0 out of 107 reviews
Rating 4 - Poor. 0 out of 107 reviews
Rating 2 - Terrible. 0 out of 107 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jonathan C.

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

10/10 Excellent

Mari M.

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

10/10 Excellent

Donald S.

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

10/10 Excellent

Jonathen A.

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

10/10 Excellent

Andrew G.

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

10/10 Excellent

Sarah B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful cottage, Tim was super responsive when I had any questions, recieved a welcome letter months ahead of time with all kinds of useful tips about the ferry/navigating the island/ checkout/ sheet rental etc. Tip: in off season the car ferry doesn't run after 530pm mondays/Tuesdays so plan accordingly! There was baby gates for the stairs, Legos, childrens books, a highchair, playpen, games, books. The cottage is thoughtfully and comfortably decorated with lots of cozy nooks for its size but simple enough that I didn't have to worry about my 1 and 3 yr olds constantly knocking something over. Highly recommend for families and enjoyed our stay! The grocery store closes at 6 but had a great selection and really good pizza (Thursday night deals) The cottage doesn't have a sea view but is very conveniently located. The bathroom is actually a comfortable size w a nice warm shower and functional curtain. Neighbors were very quiet while we were there. Renting beach towels with a local business Tim connected us to was very simple/straight forward. Would stay again:)
Stayed 5 nights in May 2026
Verified

8/10 Good

Melanie K.

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

Great location

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

10/10 Excellent

Lisa P.

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

10/10 Excellent

Zoe S.

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

10/10 Excellent

Margie W.

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

10/10 Excellent

Andrea P.

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

10/10 Excellent

Ken G.

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

8/10 Good

Michelle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We traveled to Peaks Island for a wedding so really only used the home to sleep and shower. Beds were comfortable and it was clean. It’s an older home without a lot of frills but worked well for what we needed. Communication with the host was great so we knew exactly what to expect.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Kevin S.

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

10/10 Excellent

Amanda M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What an absolutely precious time we had at this incredibly beautiful and historical space. The hosts were so helpful and kind. We could not be more grateful. We hope to return for years to come. Thank you for sharing your home!Kindly,Amanda and family
Stayed 7 nights in Aug 2025
Response from VrboOwner on 27 Aug, 2025
So glad you had a great stay. We'd love to have you back--just let us know your dates when you know them.
Verified

10/10 Excellent

Mary H.

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

10/10 Excellent

Mary B P.

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

10/10 Excellent

Sydney S.

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

10/10 Excellent

Theresa J.

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
Verified

10/10 Excellent

Stephanie B.

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

Getaway with friends

Everything was great!
Stayed 3 nights in Jul 2024
Response from VrboOwner on 5 Aug, 2024
So glad! Thanks for being great guests!
Verified

10/10 Excellent

Nicole H.

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

Perfect cottage

We very much enjoyed our stay. We found the cottage to be comfortable and as advertised. The location was great. Communication with Tim was easy, and he was super responsive.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Henry

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had to book a quick two night stay in the Portland Area and found this great little cottage. Absolutely charming. Very comfortable beds and cozy comforters. Can't beat the location. Only one suggestion -- first night was pretty cold for early October and the space heaters took a while to warm up the place. So keep an eye on the overnight temps when you pack. That said, we had a wonderful stay.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Ally P.

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

Beautiful place!

So clean, peaceful, beautiful and family friendly! We stayed with our 3 year old and 4 month old and the house was very friendly to babies and toddlers. The location is great, and hosts are very accommodating and responsive! Definitely will return!
Stayed 2 nights in May 2023
Verified

10/10 Excellent

catherine l.

Perfect cottage

The cottage is neat and not overdone, you feel very much at home, great location, sweet neighborhood, loved it all. Great week
Stayed 7 nights in Jul 2018
Response from VrboOwner on 26 Mar, 2020
Thanks so much, Kent and Catherine. We loved having you again and hope you return! It's great having great guests. Best, Tim
Verified

10/10 Excellent

Sarah B.

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

Charming house and convenient location

Charming house and convenient location a short walk from town. Host promptly & helpfully responded to questions. House was spacious and was great for a group with multiple areas to hang out, both inside and out.
Stayed 7 nights in Jun 2024

About the host

Hosted by Owner/Manager

Host profile image
My wife and I teach at a college in the Midwest but are from New England. We have two kids.

Why they chose this property

We bought this place to set down roots on the East Coast again, to reconnect our family with family and friends in the summer time and because we love Maine. We hope you will love this cottage and your time on Peaks.

What makes this property unique

Some of our favourite things about this cottage are its spaciousness and character, the quiet and friendliness of the neighborhood, and the closeness to the ferry, stores and Sandy Beach. Peaks Island itself is just so lovely and peaceful and close to the awesome city of Portland.

Languages:

English, German
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