Holiday houses in Peaks Island

4.86 out of 5 average rating, 170 reviews

Home in Portland

Booking Now: Year-Round Peaceful Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. Great biking, hiking, swimming, and kayaking.

4.98 out of 5 average rating, 135 reviews

Yurt in Chebeague Island

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

4.98 out of 5 average rating, 151 reviews

Apartment in Portland

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

Superhost

Guesthouse in Portland

4.9 out of 5 average rating, 31 reviews

Cozy guesthouse on Peaks Island by the ocean

Stay in our cozy, rustic guesthouse on Peaks Island. We‘re a block from the ocean and a short walk from the ferry and “down front” galleries, cafes, restaurants and shops. Wake up to the smell of sea spray. Walk to the beach in minutes, take a dip or beachcomb. Lounge up in the loft of our desert-meets-ocean motif, or doze on super comfy bed. Cook in the kitchenette and enjoy your meal outside on the deck. Perfect for a couple or little family. Our home is the main house.

4.93 out of 5 average rating, 629 reviews

Apartment in Portland

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Guest suite in South Portland

5 out of 5 average rating, 251 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

4.92 out of 5 average rating, 282 reviews

Guest suite in Portland

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Superhost

4.85 out of 5 average rating, 148 reviews

Artist's Retreat

A 1900's beach cottage on Peaks Island, a 5 minute walk from the ferry, but nestled off the road in a park like, peaceful setting. Hear the waves at night from the backyard, walk 5 minutes to Sandy Beach for swimming and to Picnic Point, with its view of Cushing Island and Whitehead Pass. Experience the beauty of Peaks -- but take a 17 minute ferry ride into downtown Portland for award winning restaurants. The best of both worlds!

Superhost

Apartment in Portland

4.85 out of 5 average rating, 319 reviews

East End Oasis

2bed, 1bath-1st Floor Unit. Located in the middle of Portland's most desirable neighborhood - the top of Munjoy Hill in the East End of Portland. Hardwood floors throughout. The double lot offers a LARGE and PRIVATE fenced in yard, complete with 2 patios/sitting areas, a grill, and beautifully maintained flower/vegetable gardens. Wash & Dryer in Unit. One off street parking spot and city bus stop on the street.

Guest suite in South Portland

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

4.97 out of 5 average rating, 139 reviews

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

4.95 out of 5 average rating, 133 reviews

Guesthouse in Portland

Tiny Cottage Hideaway, close to everything

A studio built in 1920 turned one-bedroom Guest Cottage, full of charm, on "Peaks Island". Within 5 minutes walking distance to the ferry, restaurants, a beach and shopping "Down Front". Perfect for 1-2 people and possibly a third. The Tiny Cottage is an off-the-beaten-path Maine experience. Peaks Island is an 18 min ferry ride from Portland.

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Popular amenities for Peaks Island holiday rentals

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Other great holiday rentals in Peaks Island

Private room in Peaks Island

4.84 out of 5 average rating, 226 reviews

Peaks Island stays with 2 night minimum

LindsayRating, 5 stars2 weeks ago

Lovely home on Peaks Island! Rhonda is such a warm, friendly host and went above and beyond to make sure we had everything we needed during our stay.

5 out of 5 average rating, 4 reviews

Dream Maine Cottage on Peaks Island

DavidRating, 5 stars48 months ago

Peaks Island is just a 15 minute ferry ride away from Portland, but once you get there you feel removed from the stress, but enough services and things to do that you're not isolated. Great place to relax and Sarah's place is a perfect island getaway.

Home in Portland

5 out of 5 average rating, 4 reviews

Sea Glass - Peaks Island oceanfront stunning views

JacquieRating, 5 stars9 months ago

Sea Glass Cottage is peaceful and inspiring in an otherworldly way. The ocean views and sea breezes, sunrise to sunset, are beyond what the pics can represent. And PSA- THE SUNSRISES!!!! Set your alarm- they’re WORTH IT! The hosts have thought of so many details- the historic and welcoming home has an incredibly well-equipped kitchen filled with lovely glassware and serving dishes. You will also find high-end and comfortable outdoor furniture, fans, tons of games and beach chairs & outdoor equipment galore. The hosts are personable, responsive, flexible and clearly very emotionally invested in this special property. It’s a legacy in the making- you will not be disappointed! Just book it- the memories you will make here will be PRICELESS!

4.91 out of 5 average rating, 22 reviews

Island Romance

ThomasRating, 5 stars9 months ago

We love older properties; this one has tons of character with a good kitchen, grill, and bathroom. Fantastic porch. Turkeys in the yard. We loved it!

5 out of 5 average rating, 122 reviews

Private room in Portland

Carrabassett Lodge

KarenRating, 5 stars9 months ago

Wow!! Mom and I loved Ella Mae’s place. So private, so comfortable, the best location to the pier and heart of things on the island, and an absolutely stunning , daily sunset view. We had such a relaxing and fun time. Ella Mae couldn’t have been any sweeter or helpful. We really loved everything about our stay at Peaks Island and Ella Mae was just a perfect host. Highly recommend.

4.62 out of 5 average rating, 26 reviews

Seaview Cottage/Quintessential Maine With a View

JamisonRating, 5 stars11 months ago

Mary is an excellent host. Very friendly, helpful and responsive. The house was not just clean and comfortable but it was obviously decorated with love and care. The Sun Room was an especially lovely place to be , with amazing views of Great Diamond and the bay…like a private tree house with lots of light. Also, the kitchen was VERY well appointed…great for cooking.. a special nod to the back deck…that’s where to find a cool breeze and a view of the very pretty gardens.