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

Guesthouse in Portland

4.95 out of 5 average rating, 300 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Guest favorite

Guesthouse in Brunswick

4.95 out of 5 average rating, 108 reviews

Apartment in Brunswick with Country Charm No Fees

This apartment is in a quiet neighborhood, surrounded by greenery and trees with a large front porch and back deck perfect for enjoying the outdoors. The apartment is bright and airy with plenty of natural light. The living room is spacious and inviting, with a large window that looks out onto the backyard. The kitchen is well-equipped with modern appliances. The master bedroom is a tranquil retreat. The backyard is private. This is the perfect place to relax and enjoy the beauty of nature.

Guest favorite

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

Guesthouse in New Gloucester

4.89 out of 5 average rating, 133 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!

Guest favorite

Guesthouse in Hiram

5 out of 5 average rating, 101 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

Guesthouse in Old Orchard Beach

4.89 out of 5 average rating, 148 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!

Guest favorite

Guesthouse in Brunswick

4.94 out of 5 average rating, 126 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 and stocked with Aesop products for your use! 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 favorite

Guesthouse in Portland

4.96 out of 5 average rating, 458 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 Portland

4.96 out of 5 average rating, 440 reviews

Spacious & Convenient 2 Bd/1 bath w/ Free Parking

Our home is close to everything Portland has to offer! We're a 5 minute drive from the airport, about 10 minutes from downtown, and walking distance to Thompson's Point to enjoy concerts, events, and libations. We are in a quiet, family friendly neighborhood with plenty of free parking. Our rental is a spacious 2 bedroom, 1 bath apartment above our garage with a private entrance. **PLEASE NOTE THERE IS NO KITCHEN** City of Portland License #001706

Guest favorite

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 173 reviews

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

Guest favorite

Guesthouse in Windham

4.99 out of 5 average rating, 251 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

Guesthouse in Cumberland

4.96 out of 5 average rating, 201 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.