Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

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

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Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

May 15 – 22

ﺩ.ﺇ514 per night

Guest favorite

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

ﺩ.ﺇ556 per night

Guest favorite

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

ﺩ.ﺇ466 per night

Guest favorite

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

ﺩ.ﺇ342 per night

Guest favorite

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

ﺩ.ﺇ445 per night

Guest favorite

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

ﺩ.ﺇ588 per night

Guest favorite

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 7 – 14

ﺩ.ﺇ360 per night

Guest favorite

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.

Dec 6 – 13

ﺩ.ﺇ509 per night

Guest favorite

Home in Lewiston

4.99 out of 5 average rating, 138 reviews

Clean and comfortable home

First floor of newly renovated, well-stocked, single-family home in quiet, safe neighborhood. Full kitchen, 2 bedrooms each with comfortable queen-sized bed, full bathroom, on-site laundry. Shoppable art on-site :) Located less than 1 mi from Bates College and St. Mary’s Hospital. Less than 2 mi from Central Maine Medical Center. Proof of Covid-19 vaccination may be requested for all eligible to receive vaccine (including children).

Jun 9 – 16

ﺩ.ﺇ423 per night

Guest favorite

Guest suite in Portland

4.91 out of 5 average rating, 197 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!

Mar 28 – Apr 4

ﺩ.ﺇ381 per night

Guest favorite

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

ﺩ.ﺇ475 per night

Guest favorite

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

ﺩ.ﺇ432 per night