Holiday rentals in Cumberland County

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Top-rated holiday rentals in Cumberland County

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Top guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 398 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 favourite

Home in Naples

4.99 out of 5 average rating, 125 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Superhost

Cabin in Raymond

4.93 out of 5 average rating, 155 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Guest favourite

Tiny home in Bowdoinham

4.91 out of 5 average rating, 116 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 favourite

Guest suite in Saco

4.96 out of 5 average rating, 158 reviews

Suite LunaSea

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

Top guest favourite

Flat in Windham

4.99 out of 5 average rating, 138 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.

Superhost

Flat in Portland

4.78 out of 5 average rating, 578 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

Top guest favourite

Guest suite in South Portland

5 out of 5 average rating, 255 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.

Guest favourite

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!

Guest favourite

Guest house in Brunswick

4.94 out of 5 average rating, 155 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

Guest favourite

Guest house in Cumberland

4.96 out of 5 average rating, 228 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.

Guest favourite

Flat in Westbrook

4.89 out of 5 average rating, 200 reviews

Cozy one bedroom on 2nd floor, close to Portland

Minimalist, boho vibe set in a vintage back drop. The trim, moldings and radiators are original to our 1890 home but with clean design you won't feel the clutter of vintage. Guests looking for a quiet retreat or calm vacation spot will enjoy. 15 minutes to Portland. 30 to LL Bean and Freeport for great shopping. Netflix etc in the room.

Holiday rentals for every style

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Flats

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

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Quaint homes, peaceful surroundings

Popular amenities for Cumberland County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cumberland County

Guest favourite

Guest suite in Freeport

4.96 out of 5 average rating, 23 reviews

Studio Apartment in Freeport

KatieRating, 5 stars1 week ago

What a great place. I cannot even think of anything that was not cool about that place. i was originally worried that the studio would be a. bit tight for 2 adults and 2 teenagers but it was enough space for all of us..The whole space was so tastefully decorated with so many personal touches. Communication was awesome...

Home in Gray

5 out of 5 average rating, 4 reviews

The Lazy Hummingbird - Little Sebago home w/ Sauna

AlbertoRating, 5 stars1 week ago

Sam's property was fantastic and was exactly as described and shown in the pictures. The lakeside location was beautiful and peaceful and the house was clean and ready for our arrival. Sam was extremely responsive with any questions I had, made it easy to check in and out, and has great taste in music if the vinyl collection is any indication. I can definitely recommend this property for anyone looking for a lakeside getaway.

Guest favourite

Flat in Gray

5 out of 5 average rating, 7 reviews

Bright and Cozy Studio

KatherineRating, 5 stars2 weeks ago

Clean beautiful little studio. Had everything you’d need including coffee! Comfortable bed and everything was very tidy and homey. Very responsive hosts as well.

Guest favourite

Guest suite in Pownal

4.97 out of 5 average rating, 96 reviews

Suite at Maine Mystic Gardens

HollyRating, 5 stars3 days ago

Family friendly. comfortable. Anna had the dishes, pans, extra toothbrush, soap to make it super easy. Very clean. Kids loved stretching their legs on the property. I loved proximity to Portland, Freeport even doable for Acadia day trip. thank-you

Top guest favourite

Guest house in Westbrook

5 out of 5 average rating, 32 reviews

Riverfront guest house w/ patio

GabrielaRating, 5 stars4 days ago

We absolutely loved Heather’s place. It’s tucked away in a really peaceful corner. She has made the inside and the outside of the guest suite extremely accommodating. The inside is very thoughtful and has everything you might need! The Airbnb was impeccable, from the construction to the cleanliness. We want to come back to Portland in the future, and won’t hesitate to stay here again!

Guest favourite

Cabin in Poland

4.86 out of 5 average rating, 44 reviews

Cozy cabin on the lake with the loons

RheaRating, 5 stars1 week ago

We had such a lovely and peaceful stay. The cabin is perfectly set back from a little road that has almost no vehicle traffic and offers the most beautiful view. Waking up to enjoy coffee on the deck with loons and bald eagles is truly special. Sunning and paddle boarding off the dock was also a real treat. Everything was very well stocked and easy to use, and all the linens and towels were nice and clean. We definitely had everything we needed. This is a wonderful little cabin and we are so happy we had the opportunity to enjoy it!

Superhost

Home in Windham

5 out of 5 average rating, 3 reviews

Lakefront | Dock + Fire Pit Near Sebago & Portland

JenniRating, 5 stars5 days ago

Beautiful lakeside property! Our family loved our weeklong stay complete with paddle boarding, cozy movie nights, and a generous welcome basket that we enjoyed for our s’mores night. Super comfy beds and cozy interior. Kevin was a fantastic host and was super responsive to all of our questions. If you’re looking for a peaceful getaway with lots to do while you unplug (or choose to stay plugged in) look no further.

Farm stay in Gray

4.84 out of 5 average rating, 309 reviews

The Retreat at Crystal Lake Farm

AmieRating, 5 stars3 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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Holiday rentals in Cumberland County

Top-rated holiday rentals in Cumberland County

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