Holiday rentals with beach access in Peaks Island

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. 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 Sept

Home in Portland

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.

7 – 14 Dec

Apartment in Portland

Clean East Bayside Apartment- Amazing Location!!

This clean and cozy apartment is walkable to everything Portland has to offer. Within minutes you can access sweeping views of the Eastern Promenade and East End Beach, as well as award winning restaurants along Washington Ave and Congress St. The Old Port and Arts District is a 20-25 min walk, and there's a plethora of art galleries and live music venues to peruse along the way; not to mention the Airbnb is walkable to 10 different breweries, 3 distilleries, 4 wineries, and 2  kombucharies.

Apartment in South Portland

Comfortable apartment near Willard Beach!

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

5 – 12 May

Cabin in Freeport

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

14 – 21 May

Apartment in South Portland

Sunny and beautiful brick house apartment

This beautiful and cozy apartment was renovated by our own hands, with energy efficiency and craft in mind. The space is an opened kitchen/living room with 2 bedrooms. Reclaimed beams and old wood mix with fun colors and gorgeous full sunlight. A lush organic garden surrounds the house with backyard chickens. Set on a quiet street, walking distance to Willard Beach & Scratch bakery, 5 minutes to Portland Headlight and 10 minutes to Portland's Old Port.

20 – 27 Oct

Guesthouse in Cape Elizabeth

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

11 – 18 Apr

Guest suite in Windham

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

13 – 20 Dec

Guesthouse in Portland

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.

5 – 12 Apr