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.

23–30 Mar

$169 SGD 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.

12–19 Nov

$287 SGD per night

Guest favourite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! Bonus: 2 super friendly dogs and a cat that will be around the property during your stay. No smoking. No pets. STHR-000718-2018

17–24 Sep

$206 SGD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 111 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!

12–19 Sep

$158 SGD 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 Sep

$147 SGD per night

Superhost

Flat in Portland

4.79 out of 5 average rating, 433 reviews

The Munjoy Hill Experience

Enjoy Portland's East End like a local with this stunning open-concept apartment as your home base! Located in the heart of Portland, you're just a walk away from the Eastern Promenade, brunch at a local favorite-The Front Room, Portland's lively night life, and so much more. The apartment easily fits two guests and features a queen bed, a mini kitchen, a family room with a tv and a bathroom. Ideal for traveling professionals, and vacationists alike.

26 Apr – 3 May

$159 SGD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 169 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.

24 Nov – 1 Dec

$185 SGD per night

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 196 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!

3–10 Nov

$138 SGD 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!

8–15 Mar

$362 SGD 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

16–23 Nov

$190 SGD 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.

18–25 Dec

$324 SGD per night

Guest favourite

Loft in South Portland

5.0 out of 5 average rating, 105 reviews

Serene studio apartment, close to everything.

Welcome to South Portland! Your spacious studio apartment with private entrance is a short walk to Fore River Brewing, Lincoln & Main/Electric Bike Cafe & Winery and the Greenbelt Walkway. A 10-min Uber ride will take you to the Old Port and South Portland staples like Willard Beach and Scratch bakery.

19–24 May

$188 SGD per night