Holiday rentals in Cumberland

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Top-rated holiday rentals in Cumberland

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Guest favourite

Guest suite in Freeport

4.96 out of 5 average rating, 186 reviews

Waterfront Private Apartment just 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

22–29 Jan

$161 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. New in 2024: A/C!!STHR-000718-2018

19–26 Sep

$211 SGD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 114 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!

22–29 Oct

$137 SGD 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.

7–14 Feb

$191 SGD per night

Guest favourite

Flat 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

1–8 Nov

$264 SGD per night

Guest favourite

Cabin in Freeport

4.98 out of 5 average rating, 471 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

12–19 Dec

$240 SGD per night

Guest favourite

Flat in Portland

4.93 out of 5 average rating, 560 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.

4–11 Dec

$132 SGD per night

Guest favourite

Home in Cumberland

4.95 out of 5 average rating, 280 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.

24–31 May

$242 SGD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 173 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.

14–21 Feb

$148 SGD per night

Guest favourite

Guest house 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.

29 May – 5 Jun

$175 SGD per night

Guest favourite

Guest suite in Windham

4.92 out of 5 average rating, 152 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.

16–23 Oct

$159 SGD per night

Guest favourite

Guest house in Cumberland

4.97 out of 5 average rating, 153 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.

7–14 Jul

$490 SGD per night