Guest house holiday rentals in Cumberland County

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Popular amenities for guest house rentals in Cumberland County

Family-friendly guest house rentals

Guest house in Brunswick
4.84 out of 5 average rating, 43 reviews

Stylish, high end, close to Bowdoin & town

ErikaRating, 5 stars79 months ago
Sarah's place is fantastic! It is adorable, quiet and extremely comfortable. It is in a wonderful location and Sarah let us know about a lot of local places. We thoroughly enjoyed our stay with Sarah, and I look forward to staying here whenever I am in Brunswick!
Guest house in South Freeport
4.99 out of 5 average rating, 93 reviews

South Freeport Village Barn

ChrisRating, 5 stars62 months ago
This is a great place to stay if you want a slice of life in the picturesque village of South Freeport, Maine. It's a very private location, and convenient for taking walks down to the water and around the village. The Airbnb itself is comfortable, quiet, and well appointed.
Guest house in Old Orchard Beach
4.9 out of 5 average rating, 10 reviews

Location Location @ Tami Lyns Place

BritneyRating, 5 stars20 months ago
The place was beautiful and the hosts were great! It was the perfect distance to be walkable to the pier, but far enough away so we had peace and privacy. Overall I highly recommend Tami’s place!
Guest favourite
Guest house in Portland
4.95 out of 5 average rating, 305 reviews

Beautiful large studio on the ocean.

MaryRating, 5 stars1 month ago
We could not have asked for a more perfect place to spend a long weekend! Hilary was kind, thoughtful and extremely communicative. She answered any questions we had and it was so nice to have a friendly face around. The space itself is perfect, it’s cozy but so spacious and bright. We loved the high ceilings and all the windows. We felt so at home the whole time. The location is also perfect, we were never more than a 10 minute drive from the things we wanted to do while also feeling nicely tucked away from the city in the evenings. We definitely hope to come back here!
Guest favourite
Guest house in Scarborough
4.98 out of 5 average rating, 112 reviews

Smith Cottage Higgins Beach

EricRating, 5 stars1 month ago
Bev was a wonderful host and the cottage was exactly what we needed - a clean and beautiful space to host the few of us who didn't have beds at my mom's place down the road during a big family gathering. The cottage has everything you could need, it's impeccably clean, quaint, and in great repair. So glad to have found Bev and the cottage (thank you again for your hospitality!), and will definitely be back again. One of the best short-term rental experiences I've had!
Guest house in Old Orchard Beach
4.85 out of 5 average rating, 27 reviews

1 Block to the Beach!

PatrickRating, 5 stars8 months ago
Wonderful place with exceptional hosts. The layout was perfect for our group of two adults and two kids. Easy 2 min walk to the beach. We all agree the best food we had on the trip came from the restaurant and shop downstairs and the best way to start our day was with a homecooked breakfast at Tami Lyns place. We hope to make this our yearly spot and would highly recommend and come again.
Guest favourite
Private room in Cape Elizabeth
4.98 out of 5 average rating, 234 reviews

Salty Air in Cape Elizabeth | Portland | Beaches

CarolRating, 5 stars1 month ago
This place is so cozy, comfortable, and attractive. The hosts have thought of everything, and the little touches are much appreciated (the paper plates and napkins, the books you can take to read, the bathroom deodorizer, the little table in the closet, etc.). We have stayed here a number of times, and it's always a pleasure!

Guest house rentals with a patio

Guest favourite
Guest house in Portland
4.97 out of 5 average rating, 30 reviews

Cozy guesthouse on Peaks Island by the ocean

DanielaRating, 5 stars5 months ago
Great little airbnb on the island. Private and easy to get to! Everything was clean and had the basic necessities. Would definitely visit again!
Superhost
Guest house in Bridgton
4.88 out of 5 average rating, 112 reviews

Private apart with luxury view, mins to everything

MarissaRating, 5 stars2 weeks ago
Loved staying in this cozy apartment. Responsive host. Beautiful view of the mountain and winter scenery!
Guest favourite
Guest house in South Portland
4.97 out of 5 average rating, 89 reviews

Willard Beach Guest House Minutes from Everything!

SheaRating, 5 stars4 months ago
John's airbnb was a very cozy little place with a great use of space that offered everything we needed for our short stay. The home is adjacent to great beach access and a wonderful bakery while being a short uber drive to downtown. Would stay again in a heartbeat.
Guest favourite
Guest house in Westbrook
5 out of 5 average rating, 26 reviews

Riverfront guest house w/ patio

ChrisRating, 5 stars3 months ago
Heather was a great host - very communicative with a simple check in/out. The guest house was nice, featuring a waterfront view. While not too far from Portland, it is about 20 minutes which is worth considering if you like to come and go a lot. The guesthouse was a quiet, peaceful place to end each of the days of our stay!
Guest favourite
Guest house in Brunswick
4.96 out of 5 average rating, 131 reviews

Apartment in Brunswick with Country Charm No Fees

HarlieRating, 5 stars6 days ago
cozy place! had a great stay:)
Guest favourite
Guest house in Yarmouth
5 out of 5 average rating, 94 reviews

Sunny guesthouse in coastal Maine

BrendaRating, 5 stars1 month ago
We stayed in this Airbnb for the third time. There are many reasons why we keep coming back. The place is gorgeous, always clean, and the hosts are friendly and helpful. It was a perfect place to stay with a toddler, they even had toys and books for him. The house is incredibly well-equipped, which is even more important during the winter.
Guest favourite
Guest house in Brownfield
4.98 out of 5 average rating, 59 reviews

The Forested Bohemian . Tiny home/ tree house

StevenRating, 5 stars5 days ago
This place is absolutely beautiful! There are so many beautiful little details that we loved about the place. It’s a work of art and felt so cozy. It was clean, warm, comfortable and felt like a home right away. The surrounding area is beautiful and it’s close to so many outdoor adventures. We stayed in the winter and the electric stove was so nice and warm! Would highly recommend staying here!
Guest favourite
Guest house in Old Orchard Beach
5 out of 5 average rating, 15 reviews

Old Orchard Oasis

KayRating, 5 stars1 month ago
Cozy, clean, great bed, good shower. We came at Christmas when it was quite cold and were thus able to access the walking trails out in back of the property without fear of ticks. Lots of small thoughtful touches and beautiful poinsettias to welcome us. Phoebe and Nathan responded immediately to our queries. Easy check-in and we felt safe. The property was quiet. Very nice stay.

Guest house rentals with a washing machine and dryer

Guest favourite
Guest house in West Bath
5 out of 5 average rating, 29 reviews

Spruce Ledge Boathouse

AshleyRating, 5 stars4 months ago
A million dollar view from the bed /living room! This was the perfect, quiet escape for a couple like us with demanding jobs. We watched the lobster boats with the provided binoculars, enjoyed a cozy fire with second-to-none sunsets and star gazing every night ! This place does have a lot of stairs to get down to the boathouse but SO worth it ! It is a bit of a trek on hilly dirt roads from town but the closest grocery stores and downtown Bath are within a 20 minute drive. Lexie was super responsive and accommodating and she gave us great recommendations for our vacation..Fred is super cool, has his own tree business and works on boats and wood working in his spare time. super nice couple !
Guest house in Oxford
4.75 out of 5 average rating, 36 reviews

Camp in the woods in a luxury RV camper

JoyRating, 5 stars5 months ago
This place was amazing and Albert and his wife are amazing host ! The things they did for us without asking made our stay even more special 😊 small fixable problems but fixed right away , we will definitely be going back again !!! Thank you again for such a niece vacation !
Guest favourite
Guest house in Scarborough
5 out of 5 average rating, 8 reviews

Guest house, dead end Prouts Neck, Scarborough

LuciaRating, 5 stars4 months ago
We had a great time at William’s home - the surrounding area was beautiful and we felt right at home. The beach is a super quick walk away, and the bird sanctuary is right out the front door. It was also easy to get into Portland each day.
Guest favourite
Guest house in Yarmouth
4.99 out of 5 average rating, 127 reviews

Private Guesthouse in the Woods

WendyRating, 5 stars2 months ago
We loved our stay at Stephanie and Denis's guesthouse! The location was great - close to Portland but also close to Freeport, ME (home of many outlets and the flagship location for the LL Bean store). Of course, you're also close to lots of water for walks on the beach. The guesthouse was immaculate and the perfect stay for me, my husband, and our two mini dachshunds. The bed was super comfortable with nice linens which was great for a good night's rest after a day out exploring. The guesthouse has lots of light with large windows but also feels private and peaceful surrounded by trees and woods. We felt right at home and were welcomed by Stephanie, Denis and their pup, Luna. We certainly cannot wait to return. It was also really nice to have a parking spot and didn't have to worry about parking in Portland. We felt this lovely guesthouse was the best of all worlds!
Guest favourite
Guest house in Freeport
4.97 out of 5 average rating, 35 reviews

Downtown Freeport Barn’acle

EricRating, 5 stars4 months ago
If this property is available for your dates, grab it. Everything was perfect, and exactly as advertised. Starting with Julia, she was pro active and great with communication. Directions to find property and get it were easy to follow. The house itself was immaculate and just the right size for the 3 of us. All the beds were very comfortable, and the location is perfect for exploring Freeport. Definitely recommend and would stay again if we're ever back to this area.
Guest house in Greene
New place to stay

Private Hilltop View

MichallaRating, 5 stars4 days ago
Was a beautiful area and the place was perfect.
Guest house in Cumberland
4.89 out of 5 average rating, 9 reviews

Charming Maine Country Cottage on Candlewick Lane

MorrisRating, 5 stars2 months ago
the space was extremely homie, we loved it! it was quite and cozy, a perfect weekend getaway. Lindsay gave us lots of recommendations on places to eat, see, and do. I would definitely stay again given the opportunity!
Guest favourite
Guest house in Gorham
5 out of 5 average rating, 37 reviews

Cozy 2BR retreat min toUSM&Sebago

AlisonRating, 5 stars4 months ago
An exquisite place to stay! We were in town for a wedding a short distance away. This AirBNB was the perfect size for 4 guests, and the location was beautiful, quiet, and private. It is stocked with every possible amenity you could imagine, including a welcome basket of local goodies and a handwritten note from the hosts. Joan (and Andy) goes/go above and beyond to make sure your every question, concern, and ask is addressed at once. As luck would have it, we experienced extremely gusty winds and not one but TWO power outages while we were there, trying to get ready for the wedding. Joan and Andy immediately made sure a generator was hooked up and we had water and electricity. In addition, she offered us a partial refund for the inconvenience. We could not have asked for a more gracious host. We would stay here again and highly recommend it to anyone traveling to this part of Maine!

Destinations to explore