Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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

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Guest favourite

Guesthouse in Portland

4.95 out of 5 average rating, 281 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

May 27 – Jun. 3

$221 CAD per night

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.

Oct. 30 – Nov. 6

$204 CAD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 113 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!

Oct. 13 – 20

$147 CAD per night

Guest favourite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Our cozy and tranquil one bedroom cottage is located in the heart of Freeport Village. Enjoy a short walk to restaurants, shops, and outlets – including the L.L. Bean flagship store steps away! Our clean and tastefully decorated cottage offers all you need and awaits your arrival. Wifi & Cable TV in Living Room & Bedroom. We THE COTTAGE DOES NOT ACCOMADATE CHILDREN UNDER THE AGE OF 12 FOR SAFETY REASONS. WE DO NOT ACCEPT GUESTS WITH NO REVIEWS ON AIRBNB. NO PETS DUE TO SEVERE ALLEGIES.

Jan. 11 – 18

$217 CAD per night

Guest favourite

Loft in Freeport

4.97 out of 5 average rating, 194 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Cable, Netflix, Disney Plus, Hulu and Amazon). Very comfortable queen size bed with floor space for kids if desired. Fantastically located just over a mile from beautiful Winslow Park's walking trails and beach, four miles south of downtown Freeport's shopping and 15 miles north of the popular city of Portland. Housebroken and well behaved pets welcome to join their humans!

Jun. 8 – 15

$238 CAD per night

Guest favourite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Welcome to our spacious 1000 sq. ft. Maine barn apartment! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the private bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Apr. 6 – 13

$285 CAD per night

Guest favourite

Apartment in South Portland

4.95 out of 5 average rating, 167 reviews

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.

May 5 – 12

$198 CAD per night

Guest favourite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

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

May 14 – 21

$250 CAD per night

Guest favourite

Yurt in Cumberland

4.94 out of 5 average rating, 154 reviews

Tree Yurt

The Tree Yurt is quite literally a yurt in the trees. Surrounded by nature, this is YEAR ROUND glamping close to Portland. There is no running water except an outdoor sink in the warmer months. Typically May through October. A main house sits closer to the driveway and There is a chance the house and the yurt will be rented out at the same time. The yurt is about 200 feet from the house and the only shared space is the driveway, so it is actually very private.

Nov. 17 – 24

$190 CAD per night

Guest favourite

Apartment in Portland

4.93 out of 5 average rating, 556 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.

Nov. 26 – Dec. 3

$154 CAD per night

Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 219 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Jun. 23 – 30

$199 CAD per night

Guest favourite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

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.

Nov. 8 – 15

$182 CAD per night