Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

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Top guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 395 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

Guest favorite

Apartment in Westbrook

4.94 out of 5 average rating, 131 reviews

Peaceful 1BR | Reading Nook | Near Portland

Welcome to this bright and charming 2nd-floor apartment in a beautifully renovated 1890s home! Located in the heart of Westbrook, you'll be just a short drive from the excitement of Portland. Step outside and explore local shops, cafes, and restaurants that make the area a growing cultural hub. Enjoy scenic walks along nearby trails or visit the riverfront just minutes away. Easy access to Portland's dining, galleries, and entertainment, you’ll enjoy the perfect balance of peace and city life!

Superhost

Loft in Portland

4.9 out of 5 average rating, 294 reviews

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 140 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Top guest favorite

Apartment in Yarmouth

4.96 out of 5 average rating, 139 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Top guest favorite

Guesthouse in Cumberland

4.96 out of 5 average rating, 115 reviews

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

Guest favorite

Tiny home in Bowdoinham

4.91 out of 5 average rating, 115 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Top guest favorite

Apartment in Windham

4.99 out of 5 average rating, 136 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Guest favorite

Guest suite in Portland

4.92 out of 5 average rating, 282 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!

Top guest favorite

Tiny home in Portland

4.96 out of 5 average rating, 478 reviews

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 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 a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

Guest favorite

Guesthouse in Cumberland

4.96 out of 5 average rating, 224 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.

Top guest favorite

Farm stay in Gray

4.95 out of 5 average rating, 281 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

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Popular amenities for Cumberland County vacation rentals

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Other great vacation rentals in Cumberland County

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 20 reviews

Studio Apartment in Freeport

SheilaRating, 5 stars1 week ago

Dustin and Brianna's home is absolutely beautiful! We had excellent communication from start to finish, including a proactive text warning about a small construction project. The furnishings and fixtures are all high-quality and stylish, creating a cozy, "quiet luxury" atmosphere. The built-in bed was a hit and very delightful. The work Dustin has done is top notch and full of very careful & thoughtful detail (amazing tile work, well-placed outlets; high quality cabinets, even edge trim detail on the tiled spaces, plus more!). Not in the least, the location provides a very welcome respite from the relative craziness of downtown Freeport, with lots of privacy and beautiful nature. Absolutely recommend.

Top guest favorite

Cabin in Freeport

5 out of 5 average rating, 49 reviews

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean

MichaelRating, 5 stars1 week ago

We were in awe as we walked into the Maine Frame - the photos are gorgeous and even they don't do it justice. What a beautiful and intentionally built cabin. We loved the spaciousness of both the inside and the outside: the high ceilings, huge windows, and large deck - all were just wonderful. The water softener system was such a delightful surprise! We loved how accessible the cabin is to downtown Freeport and had fun checking out all of the shops. We also had a beautiful drive to Harpswell for a delicious meal at the Dolphin Marina & Restaurant, and got to walk around Brunswick as well. We highly recommend the Maine Frame!

Top guest favorite

Home in Windham

5 out of 5 average rating, 31 reviews

Maine Vacation Home on the Water

SamRating, 5 stars2 days ago

Kate’s place is in a beautiful location and has so much to do. We loved the wildlife, the easy access to Portland and all the yard games. We can’t wait to come back!

Top guest favorite

Cottage in Windham

5 out of 5 average rating, 79 reviews

Romantic waterfront cottage for two in Maine

MackRating, 5 stars3 weeks ago

We stayed at the cottage for a little celebratory getaway. Although the weather only partially complied, we were amazed by the beautiful views that surrounded the cottage. We spent some time exploring the area and there are some spectacular little gems hidden throughout and around Windham. Maryellen and Bryan were so sweet and made sure to make this stay feel a little closer to home. Definitely a “don’t miss” property!

Top guest favorite

Guesthouse in Yarmouth

4.99 out of 5 average rating, 140 reviews

Private Guesthouse in the Woods

RachelRating, 5 starstoday

We had a great stay here! The place was perfect location and in a very nice area. Very quiet and close by to a lot of things. Also, very clean!

Top guest favorite

Guesthouse in Westbrook

5 out of 5 average rating, 29 reviews

Riverfront guest house w/ patio

GabrielleRating, 5 stars1 week ago

Heather was a great host and made check in easy. Very cute place and perfect for two people. Would recommend staying here.

Superhost

Home in Windham

4.7 out of 5 average rating, 67 reviews

The "Happy Hen House" cottage in lakes region

MattRating, 5 stars8 months ago

As Mainer living across the country, it is always nice to come. Unfortunately this trip was to attend my Mom's funeral. Pam's home was the right level of closeness to the rest of my family to make visiting easy. The place was the peaceful retreat I needed to visit with myself. Five minutes to most things a person living out of a suitcase could need. Also less then 5 minutes walk puts one at the boat launch for personal watercraft. A great place to sit for a few. The amenities were plentiful at the house and the character was Maine charming. Pam was wonderful and easy to communicate with at all stages. I will be back in the future. Matt

Farm stay in Gray

4.84 out of 5 average rating, 308 reviews

The Retreat at Crystal Lake Farm

AmieRating, 5 stars2 weeks ago

Jonathan was very communicative and a great host. Depending on needs I would stay here again. We were there for a graduation at Bates College. I would recommend this place for fall stays, hikes or visiting the near by lake. It's kind of far from Bates and Portland to make it super convenient to visit those places. Overall it was a very good value and Jonathan was a fantastic host, oh and the place was clean.

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Vacation rentals in Cumberland County

Top-rated vacation rentals in Cumberland County

Vacation rentals for every style

Popular amenities for Cumberland County vacation rentals

Other great vacation rentals in Cumberland County

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