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Classic turn of the century Maine cottage

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Libby Cottage
The Garden
Come in!
Living room
Living Room

Reviews

10 out of 10
Exceptional
4 bedrooms1+ bathroomSleeps 8

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Outdoor space
  • Parking available
  • Barbecue

Explore the area

View map
Portland, ME
  • Place, Battery Steele
    ‪19 min walk‬
  • Place, Umbrella Cover Museum
    ‪3 min drive‬
  • Place, Fifth Maine Museum
    ‪4 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪39 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Downstairs bedroom

1 Double Bed

Master bedroom

1 Queen Bed

Upstairs bedroom

2 Single Beds

Upstairs bedroom

1 Queen Bed

1 bathroom, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

Classic turn of the century Maine cottage

Come experience Maine island living in this beautifully preserved turn of the century home. Libby Cottage is located in a quiet section of Peaks Island with a wraparound porch overlooking sunset views. You'll find an abundance of charm here with enough modern conveniences to ensure a relaxing and rejuvenating visit that you won't want to end. Libby Cottage has everything you need for an enjoyable stay - linens, plenty of warm blankets, towels, a washer/dryer, a fully equipped kitchen, an outdoor shower, a large yard, and a large wrap around porch with hammocks, plenty of seating and table/chairs.

Leave the house and turn left to a boat club with tennis courts and beach or turn right for a walk along open ocean and rocks. Both just a few minutes walk away! There's much to explore on this island by foot or by bike and if you've never been to Peaks Island before, you will quickly realize this is a place to visit over and over again. The ferry landing in town is just 1.2 miles away where there are several restaurants, a well stocked grocery store, an ice cream shop, bike rental, a library and many summer activities.

Ferries to and from Portland run hourly throughout the day and late into the night. Portland is a city of great restaurants, museums, shopping, parks and nightlife all within an easy walk from the ferry terminal.

Maine license number STHR-002023-2019.

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House Rules

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

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights
Check out is at 10 am
Safe travels home!
Failure to complete these may result in a negative review from the host.
If renting Libby Cottage for more than 2 weeks, there is a 90 day cancellation policy for full refund.
Rental of Libby Cottage during the months of July and August is Sunday to Sunday. Off season rental checkin and checkout is flexible.

Important information

You need to know

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
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

We should mention

A car is not required for transport to and from this property

About the area

Peaks Island

Located in Peaks Island, this holiday home is near the beach. The area's natural beauty can be seen at Crescent Beach State Park and Two Lights State Park, while Richard Boyd Art Gallery and Umbrella Cover Museum are cultural highlights. Travelling with kids? Consider Maine Narrow Gauge Railroad, or check out an event or a game at Merrill Auditorium. Fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain biking and horse riding nearby.
View more Holiday homes in Peaks IslandOpens in a new window
Map
Portland, ME

What's nearby

  • Battery Steele - 19 min walk - 1.7 km
  • Battery Steele - 19 min walk - 1.7 km
  • Umbrella Cover Museum - 3 min drive - 1.8 km
  • Richard Boyd Art Gallery - 3 min drive - 1.8 km
  • Fifth Maine Museum - 4 min drive - 2.2 km

Getting around

  • Portland Transportation Center - 45 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 61 min drive

Restaurants

  • ‪Second Rodeo Coffee - ‬35 min drive
  • ‪Twelve - ‬30 min drive
  • ‪North43Bistro - ‬35 min drive
  • ‪Brickyard Hollow Brewing Company - ‬29 min drive
  • ‪Scratch Baking Co. - ‬35 min drive

Frequently asked questions

Is Classic turn of the century Maine cottage pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Classic turn of the century Maine cottage ?

As of 1 Apr 2026, prices found for a 1-night stay for 2 adults at Classic turn of the century Maine cottage on 31 Dec 2026 start from AU$443, 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 turn of the century Maine cottage ?

On-site parking is available at the property.

What time is check-in at Classic turn of the century Maine cottage ?

Check-in begins at 3:00 PM.

What time is check-out at Classic turn of the century Maine cottage ?

Checkout is at 10:00 AM.

Where is Classic turn of the century Maine cottage located?

This family-friendly Peaks Island holiday home is located by the ocean, within 1 mi (2 km) of Casco Bay, Richard Boyd Art Gallery and Umbrella Cover Museum. Fifth Maine Museum is 1.5 mi (2.4 km) away.

Reviews

10

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. 19 out of 19 reviews
Rating 8 - Good. 0 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Peaks house, classic in every way.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Ardith P.

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

A classic, Peaks Island cottage

It is functional with a beautiful porch and everything you need for an amazing week. The host is very helpful with easy and quick communications. Location is great— away from ferry dock but a short cart drive to center of town. We had a great stay.
Stayed 7 nights in Jun 2019
Response from VrboOwner on 18 Aug 2023
Glad you enjoyed your week at Libby Cottage!
Verified

10/10 Excellent

Tori C.

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

Perfect stay!

Staying at Libby Cottage was a wonderful experience! The beds were very comfortable, it was easy to get in and out, and Paula had everything we could need if we forgot anything. We enjoyed many coffees and drinks on the porch during our downtime. I would recommend anyone that was coming to Peaks to stay at the cottage and enjoy a little vacation away from the grind, spent on a slow, steady island time!
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

kim and Noel D.

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

Peaceful comfortable lovely spot for relaxing and unwinding

Great owners! great location !comfortable home well equipped and a genuine Peaks home. Close to beaches ,, quiet and fabulous porch! Owners are experienced sailors and offer a sailing tour around the Casco Bay that is scenic and enjoyable!
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

Jean D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Libby Cottage! It was so close to the nicest beach & fun sailing/tennis club. We liked being far enough away from the ferry dock that you didn't notice the large number of day trippers coming in from Portland every hour. We had considered not bringing the car over, but it was pouring rain upon arrival so we decided not to try to walk or rent a golf cart. We were glad to have the car - walking for groceries or dinner would have been too far. It was a completely relaxing stay & wonderful experience!
Stayed 7 nights in Jul 2025
Response from VrboOwner on 27 July 2025
So glad to hear that you enjoyed Libby Cottage and our wonderful island - you are welcome to return anytime!
Verified

10/10 Excellent

Ethan B.

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

Paradise on Peaks

Libby Cottage is a quintessential, seasonal Maine camp/property situated on the charmed Peaks Island. We loved our time at the cottage, neighborhood, and in/around Portland. We would absolutely recommend a stay here and would love to make a return trip to Peaks at some point in a future summer. As a host, Paula was friendly, accommodating, and very easy to communicate with.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Margaret E.

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

Good memories

We had a wonderful time on Peaks Island. Peaks Island is a special place to me as my maternal grandfather’s family was one of the first families to settle on the island. The Libby cottage reminded me of my grandparents house on the island. My grandchildren loved the cottage. They played a lot of ping pong in the spacious yard. The porch was a lovely place to sit and spend time. The host was very nice and came and introduced herself to us. An added feature was sheets and towels were provided. Its a wonderful house to rent for a Peaks Island vacation.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 22 Aug 2024
Thanks for your kind review- so glad you enjoyed your stay at Libby Cottage, we would be happy to have you return!
Verified

10/10 Excellent

Andrea L.

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

Three generations at LIbby Cottage

Our first delightful surprise was the outdoor ping pong table.! The front porch was a favorite of mine..My 73 yrs. young self fit just right in the net swing .. great for reading, relaxing and meeting dogs and their people walking by the house. very well stocked home from paper to linens and everything thing else you could possibly need. .Highly recommend Libby Cottage life. Andrea L ..
Stayed 14 nights in Jul 2023
Verified

10/10 Excellent

Rosemary S.

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

Wonderful stay on beautiful Peaks Island

My husband and I rented Libby Cottage in mid-June and enjoyed every minute! One of our daughters was with us the whole time, one joined with her husband and almost 2 year old son for a few days and another daughter lives in Portland and visited a few days after work and we all enjoyed our time there. The beds are all comfortable, the shower has good pressure and temperature. The kitchen is well supplied. It is a very comfortable, quirky, inviting cottage! The porch is AMAZING, we enjoyed it in the sunshine and in the rain! And the location is perfect for us. Right up the road from the beach and sailing club and we enjoyed walking to the shops and stores in the center as well as biking around the island daily. Paula was easy to reach and really thought of everything in the planning and preparing of the cottage. There was a thunderstorm while we were on the island and she was quick to respond and keep us in the loop re: the WiFi. Great hosts. Great cottage. Great vacation!
Stayed 5 nights in Jun 2024
Verified

10/10 Excellent

Bonnie W.

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

Friends Getaway

Look rustic cabin was an authentic Maine experience. Cozy and comfortable and clean. Perfect place for hiking and biking, eating, relaxing, and just enjoying good friends!
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Ellen M.

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

Step back in time

This was the most relaxing, fun, and happy vacation I’ve had in many years, maybe ever!-Plenty of room, vintagy feels and just a little off the beaten path-the sound of birds singing, folks pedaling bikes and a couple of old horses clip-clopping past the wrap-around porch each morning while sipping coffee fed my soul…in a word:Devine !👍🏼We’ll be back to Libby Cottage very soon!
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Robert G.

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

Fantastic Cottage on Peaks Island!

We had a wonderful stay at Libby Cottage on Peak's Island! Everyting was exactly as advertised. The location is fantastic, the porch is dreamy, and Paul was an excellent host!
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Donalee S.

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

Six week stay - vacation and remote work

We had the pleasure of enjoying Libby Cottage for 6 weeks. It was a combination of some vacation and virtual work. The wifi was outstanding; we had as many as 3 adults working virtually at the same time with no slowness at all. The cottage was comfortable even with 6 adults staying there at one time. Paula was fantastic and was very helpful and responsive. The location is really ideal; with waster views, sunsets, a large porch and yard. I highly recommend Libby Cottage.
Stayed 45 nights in Aug 2020
Verified

10/10 Excellent

Donna L.

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

Peaks Island Perfect

Loved the vintage feel for the cottage, perfect location. We could see the bay from the great porch. Lovely garden out front, easy access to all the island by bike or car and the ferry worked out perfectly. The house was clean and the yard was great for the little ones.
Stayed 7 nights in Jul 2019
Response from VrboOwner on 18 Aug 2023
So happy that you and your family had a fun week at Libby Cottage and enjoyed Peaks Island!
Verified

10/10 Excellent

kate m.

Charming getaway with magical porch

We couldn't have asked for a better home/property to unwind with our three little kids for the week. The beds are comfortable, the porch is the perfect place to relax, and the house is only a short walk from a quiet little beach with the most amazing sunsets. A wonderful place to explore the beauty of Peaks Island.
Stayed 7 nights in Aug 2018
Response from VrboOwner on 18 Aug 2023
So glad you enjoyed the cottage and the family vacation-you are welcome back anytime!
Verified

10/10 Excellent

lynn k.

Beautiful cottage

Libby cottage met all our needs and the location was perfect. Lynn
Stayed 7 nights in Aug 2018
Response from VrboOwner on 18 Aug 2023
We enjoyed meeting your wonderful family and would be delighted to have you as a return guest! Thanks for leaving the cottage in such excellent condition.
Archival

10/10 Excellent

Ben Y.

Perfect Peaks Island getaway

This house was exactly what we were hoping for for a long weekend on Peak's Island. We were a group of 6 friends and the place was a perfect size for us. The beds were very comfortable (which believe me, is hard to come by in a lot of older houses) and the bedrooms all were so cozy and well designed. The house is in great condition while still maintaining it's classic Maine charm. When you think of a cottage in Maine, this is what you're hoping for. The hosts so really helpful, they live right down the street so they were available whenever we had questions. Paula even baked us some fresh bread for our arrival! I would 100% recommend staying here. We're planning on coming back next year already.
Archival

10/10 Excellent

Rev. Ryan N.

Very nice.

Nice location, friendly but not intrusive owners. Would definitely consider staying there again.
Stayed 7 nights in Aug 2017
Archival

10/10 Excellent

Libby Cottage is clean, spacious, beautiful, and has a great view.

Paula and Steve are great hosts! 8 of us booked the cottage for a long weekend with friends, and had a wonderful time. The cottage is spacious, with all the necessary accommodations. It's a close walk to the beach, has a backyard for lawn games and a great porch for enjoying coffee at sunrise and wine at sunset. Peaks Island is gorgeous, and this was the perfect place to stay. Highly recommended!
Stayed 4 nights in Jun 2017

About the host

Hosted by paula chessin

Host profile image
We bought our home on Peaks Island 12 years ago and loved it enough to move here full time when we retired in 2017. We bought this rental property 4 years ago knowing it would make a wonderful place for family and friends to enjoy the island and each other. We think the cottage is homey, comfortable and inviting and we hope you will enjoy your stay here!



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