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

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.

Mar. 2 – 9

$204 CAD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 112 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!

Sep. 26 – Oct. 3

$186 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.

May 2 – 9

$193 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. 11 – 18

$286 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!

Jul. 22 – 29

$236 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

$251 CAD per night

Guest favourite

Home in Cumberland

4.95 out of 5 average rating, 279 reviews

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a family to stay and the rental is the entire home.

Feb. 11 – 18

$316 CAD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 170 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.

Nov. 7 – 14

$205 CAD per night

Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 218 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.

May 28 – Jun. 4

$200 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.

Dec. 29 – Jan. 5

$183 CAD per night

Guest favourite

Guesthouse in Cumberland

4.97 out of 5 average rating, 152 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

May 17 – 24

$344 CAD per night

Guest favourite

Guest suite in Freeport

4.95 out of 5 average rating, 197 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

$109 CAD per night