Guesthouse vacation rentals in Cumberland County

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Top-rated guesthouse rentals in Cumberland County

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

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Guest favorite

The entrance features a modern door framed by two light fixtures, casting gentle shadows. A small potted plant enhances the welcoming feel. The house is adorned with white siding and showcases large windows, providing a sense of brightness.

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)

Guest favorite

A two-story boathouse with a rustic wooden exterior and large windows faces the water. A wooden dock extends from the structure, leading to the shoreline. Surrounding trees provide a natural backdrop, enhancing the retreat-like setting.

Guesthouse in New Gloucester

4.88 out of 5 average rating, 138 reviews

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Top guest favorite

The modern guesthouse is shown against a twilight sky, featuring a sleek exterior in muted grey tones. Snow blankets the ground around the structure, while the entrance displays wide glass doors and a spacious balcony above. Lush greenery is visible in the background.

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!

Guest favorite

A sandy pathway is visible, leading through tall beach grass toward the ocean. The calm sea reflects a clear sky, creating a peaceful coastal scene. Gentle waves can be seen in the distance, suggesting a tranquil beach experience.

Guesthouse in Old Orchard Beach

4.9 out of 5 average rating, 164 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 favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 459 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. Enjoy the trails in the woods with spectacular views or walk on the beach at one of the state parks! So beautiful!

Top guest favorite

A spacious patio area is shown, featuring various seating options including chairs and a picnic table. A swimming pool is visible nearby, surrounded by a white fence. The entrance to the bungalow is accessed from the patio, offering a scenic view of the lawn and landscaping.

Guesthouse in Portland

4.96 out of 5 average rating, 500 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 favorite

Guesthouse in Naples

4.96 out of 5 average rating, 189 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 favorite

A cozy living area features a comfortable gray sofa arranged near a light wooden coffee table. A large TV displays a streaming service, while natural light enters through expansive windows adorned with soft curtains. A small kitchenette is visible in the background.

Guesthouse in Brunswick

4.94 out of 5 average rating, 151 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 favorite

A shaded patio area features a white gazebo with a wicker table and chairs set on a wooden deck. Behind, a picturesque landscape showcases lush green foliage and an expansive field, all under a vibrant sunset sky filled with soft orange and pink hues.

Guesthouse in Windham

4.99 out of 5 average rating, 256 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 favorite

A quaint white cottage is framed by lush greenery and a flowering garden. A stone pathway leads to the entrance, bordered by smooth pebbles. Underneath a crabapple tree, a small outdoor bistro table set is seen, inviting guests to enjoy nature.

Guesthouse in Cumberland

4.96 out of 5 average rating, 220 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

A serene bedroom is visible through an open door, featuring a spacious bed draped with a light green quilt. Natural light enters from a large window, and wooden beams enhance the contemporary yet rustic feel of the space.

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 favorite

A cozy living area features large windows allowing natural light and a view of the surroundings. A dark couch is paired with a light area rug, and a small dining table with stools stands nearby. A wall-mounted air conditioning unit is visible.

Guesthouse in Portland

4.95 out of 5 average rating, 132 reviews

Tiny 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.