
Guesthouse vacation rentals in Cumberland County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Cumberland County
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Cumberland County guesthouses
Family-friendly guesthouses

Stylish, high end, close to Bowdoin & town
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!

South Freeport Village Barn
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.

Location Location @ Tami Lyns Place
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!

Beautiful large studio on the ocean.
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!

Smith Cottage Higgins Beach
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!

1 Block to the Beach!
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.

Salty Air in Cape Elizabeth | Portland | Beaches
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!
Guesthouses with a patio

Cozy guesthouse on Peaks Island by the ocean
Great little airbnb on the island. Private and easy to get to! Everything was clean and had the basic necessities. Would definitely visit again!

Private apart with luxury view, mins to everything
Loved staying in this cozy apartment. Responsive host. Beautiful view of the mountain and winter scenery!

Willard Beach Guest House Minutes from Everything!
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.

Riverfront guest house w/ patio
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!

Apartment in Brunswick with Country Charm No Fees
cozy place! had a great stay:)

Sunny guesthouse in coastal Maine
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.

The Forested Bohemian . Tiny home/ tree house
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!

Old Orchard Oasis
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.
Guesthouse rentals with a washer and dryer

Spruce Ledge Boathouse
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 !

Camp in the woods in a luxury RV camper
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 house, dead end Prouts Neck, Scarborough
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.

Private Guesthouse in the Woods
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!

Downtown Freeport Barn’acle
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.

Private Hilltop View
Was a beautiful area and the place was perfect.

Charming Maine Country Cottage on Candlewick Lane
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!

Cozy 2BR retreat min toUSM&Sebago
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
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals New England
- House rentals New England
- Guesthouse rentals Maine
- House rentals Maine
- House rentals New Hampshire
- Guesthouse rentals New Hampshire
- Guesthouse rentals Connecticut River
- House rentals Connecticut River
- Rentals with a hot tub Cumberland County
- Serviced apartment rentals Cumberland County
- Waterfront rentals Cumberland County
- House rentals Cumberland County
- Cottage rentals Cumberland County
- Monthly Rentals Cumberland County
- Rentals with outdoor seating Cumberland County
- Condo rentals Cumberland County
- Cabin rentals Cumberland County
- Rentals with lake access Cumberland County
- Ski-in/ski-out rentals Cumberland County
- Tiny house rentals Cumberland County
- Townhouse rentals Cumberland County
- Rentals with an accessible height toilet Cumberland County
- Rentals with beach access Cumberland County
- Rentals with pools Cumberland County
- Rentals with an EV charger Cumberland County
- Rentals with breakfast Cumberland County
- Kid-friendly rentals Cumberland County
- Fitness-friendly rentals Cumberland County
- Rentals with a patio Cumberland County
- Smoking-friendly rentals Cumberland County
- Yurt rentals Cumberland County
- Pet-friendly rentals Cumberland County
- Family-friendly rentals Cumberland County
- Rentals with a fireplace Cumberland County
- Private suite rentals Cumberland County
- Rentals with a sauna Cumberland County
- Rentals with a washer and dryer Cumberland County
- Rentals with a firepit Cumberland County
- Bed and breakfasts Cumberland County
- Rentals with a kayak Cumberland County
- Apartment rentals Cumberland County
- Beachfront rentals Cumberland County
- Villa rentals Cumberland County
- Farmstay rentals Cumberland County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Things to do United States
- Sightseeing United States
- Sports activities United States
- Entertainment United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Things to do Maine
- Nature and outdoors Maine
- Sports activities Maine
- Things to do Cumberland County
- Sports activities Cumberland County
- Art and culture Cumberland County
- Nature and outdoors Cumberland County