Guesthouse holiday rentals in Cumberland County

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Top-rated Guesthouses in Cumberland County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Portland

4.92 out of 5 average rating, 209 reviews

Bright, spacious, modern, newly designed suite.

Bright, modern, garden level suite with unique design features in Portland’s desirable Oakdale neighborhood. Close to the Old Port, Thompson Point Concert Hall. Family friendly location on a dead-end street, tucked away from the downtown but less than a mile away. The apartment has its own private entrance, wine bar, kitchen and bathroom with lots of unique art work. Come enjoy! Full disclosure: older house, with young kids upstairs, you occasionally will hear steps and movement (minimal)

Top Guest favourite

Guesthouse in Cumberland

4.95 out of 5 average rating, 109 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.

Top Guest favourite

Guesthouse in Hiram

5 out of 5 average rating, 111 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Top Guest favourite

Guesthouse in Harpswell

4.95 out of 5 average rating, 457 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, spacious, colorful, comfy, bright! New king bed! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away. Get out in the snow and enjoy the trails in the woods or walk on the beach at one of the state parks! So beautiful!

Guest favourite

Guesthouse in Old Orchard Beach

4.89 out of 5 average rating, 156 reviews

Adorable 2 bedroom cabin only 50ft from Beach no.7

This quaint two-bedroom cottage sleeps up to six people and offers an open kitchen, dining, living room area with cathedral ceiling. There are two roomy bedrooms, one with a queen bed and one with two bunk beds. The bathroom offers his & her sinks, shower and whirlpool tub. Conveniences inc. Smart TV, Wi-Fi, individually controlled heat and air conditioning, fully equipped efficiency kitchenettes, and private baths. Enjoy the privacy of your own seaside cottage close to the beach!

Top Guest favourite

Guesthouse in Portland

4.96 out of 5 average rating, 477 reviews

Romantic Bungalow with Hot Tub, Pool & Parking

The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Guest favourite

Guesthouse in Naples

4.96 out of 5 average rating, 188 reviews

Downtown Naples guesthouse. Steps from causeway

In the heart of Naples you will find this large 2 bedroom carriage house newly constructed in 2018, only steps away from the lakes, causeway, restaurants, grocery store and marinas. Each large bedroom has a queen bed, the kitchen is fully equipped, the television has Roku for cable access or streaming channels. There is a large deck overlooking a vacant lot. WIFI is included. Oxford Casino, Shawnee Peak, and Fryeburg Fairgrounds are all within half hour drive.

Guest favourite

Guesthouse in Brunswick

4.94 out of 5 average rating, 140 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.

Top Guest favourite

Guesthouse in Windham

4.99 out of 5 average rating, 255 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.

Guest favourite

Guesthouse in Cumberland

4.96 out of 5 average rating, 211 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

Guesthouse in Topsham

4.97 out of 5 average rating, 236 reviews

Brunswick Riverfront Garden Cottage

Facing Brunswick across the river, Bowdoin College, ocean beaches, fishing, kayaking, canoeing, restaurants. Love how it is situated, among beautiful gardens, on the river. And the two room post and beam cottage, contemporary and antique furniture. New kitchenette, new bath. Two wonderful bedrooms. Deck, barbecue, picnic table. In historic district.

Guest favourite

Guesthouse in Portland

4.95 out of 5 average rating, 132 reviews

Tiny Island Cottage Hideaway, close to everything

A studio built in 1920 turned one-bedroom Guest Cottage, full of charm, on "Peaks Island". Within 5 minutes walking distance to the ferry, restaurants, a beach and shopping "Down Front". Perfect for 1-2 people and possibly a third. The Tiny Cottage is an off-the-beaten-path Maine experience. Peaks Island is an 18 min ferry ride from Portland.