Holiday rentals in Peaks Island

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Top-rated holiday rentals in Peaks Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

6–13 Feb

£121 per night

Guest favourite

Flat in Portland

4.91 out of 5 average rating, 379 reviews

Private Hill Top Apartment Two/On Street Parking

Neighborhood of restaurants,coffee shop, variety/sandwich shop, bakery. Five minute walk to Eastern Prom. Ten to fifteen minute walk to downtown and Portland's Old Port. On bus line. Do not refer to children 12 or under as a third or fourth party to not incur the up charge for additional adults. No pets., support animals only. $60 per night. Pet not to be left alone in apartment. Note: No TV. Babysitting sometimes available, reserve date. City of Portland registration STHR-002650-2023

17–24 Apr

£127 per night

Guest favourite

Home in Portland

4.85 out of 5 average rating, 145 reviews

Hope Cottage, 4-Season Getaway, Sleeps 6

*Quiet and Peaceful *Quick 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.

5–12 Mar

£199 per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 109 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

10–17 Sept

£110 per night

Superhost

Flat in Portland

4.78 out of 5 average rating, 303 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

5–12 Mar

£105 per night

Guest favourite

Flat in Portland

4.93 out of 5 average rating, 551 reviews

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.

20–27 Nov

£92 per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 168 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.

17–24 Jan

£97 per night

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 195 reviews

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!

25 Jan – 1 Feb

£98 per night

Superhost

Cottage in Portland

4.84 out of 5 average rating, 126 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!

5–12 Mar

£248 per night

Guest favourite

Flat in Portland

4.94 out of 5 average rating, 452 reviews

No cleaning fee! Location, location! And parking!

At Location Location! You can be assured that we take care of all the cleaning… so please be on vacation! This lovely, simple 1 bedroom apartment is in the heart of the Portland's West End. Just around the corner, a foodie paradise! The Danforth bar, Chaval, Pan Men Miyake, Tandem bakery and Local 188 many others. Just down the street, Maine Med,Mercy Hospital, PMA, art galleries, shopping & the Old Port!

5–12 Mar

£87 per night

Guest favourite

Flat in Portland

4.96 out of 5 average rating, 151 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

13–20 Nov

£130 per night

Guest favourite

Guest house in Portland

4.95 out of 5 average rating, 106 reviews

Tiny Island Cottage Hideaway, close to everything

Recently remodeled one-bedroom guest cottage built in 1920 and full of charm. Within 5 minutes (walking distance) to the ferry, restaurants and shops "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 a 20 min ferry ride from Portland.

30 Dec – 6 Jan

£223 per night