
Guest house holiday rentals in Cumberland County
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Top-rated guest house rentals in Cumberland County
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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!

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.

King Size Bed Guest Room at the Harraseeket Inn
This was a WONDERFUL 5 Star Airbnb experience. The Inn is historic, well-established, and charming in every way. The staff was courteous, the place was very clean and very neat. There is plenty of parking, two places to eat on site, including a Tavern that has a great local Portland Maine beer, very good wine and some wonderful food. It's a creative menu that satisfied all. The Inn has many rooms, ours had a King size bed and a Jacuzzi. Nice! The bed linens were seriously soft, the bed very, very comfy. It was very quiet too. Had a great night sleep. The on-site lap pool was delightfully warm. The Inn is a short walk to LL Bean, open 24 hours, so if you're a hiker, biker, kayaker or love the outdoors, that's a plus. The stay included a very nice buffet breakfast, lots of omelettes, oatmeal, fresh fruit, organic coffee, bacon and much more. It also includes afternoon tea, we arrived too late for that. We were here for only one night, we wished we had more time to hangout. We highly recommend Harraseeket Inn in Freeport ME. Of special note is the excellent communication skills of their General Manager, Chip Gray. He emailed, texted and promptly answered all our prestay questions. He's great at what he does! Thanks, Harraseeket Inn. We'll be back!

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.

Salty Air in Cape Elizabeth | Portland | Beaches
Sherry &John are wonderful hosts. The AirBnB is comfortable, clean, quiet and very welcoming to all that stay. Being 20 minutes from downtown Portland we had the best of Maine. Thank you, Sherry and John, our 5 star hosts!!

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!

Queen bed suite; lake region!
Guest house rentals 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
My favorite Airbnb stay so far. My family and I travel frequently. I am originally from Maine and we came back for spring break. Linar’s home was exceptional. Everything you needed was available, from cooking to bathroom necessities. It snowed for a day on our stay making for incredible views of the mountains and pine trees. The apartment feels just like a cabin experience, and you can see and feel the love that went into it. I can’t say enough wonderful things about our stay! The couch bed was comfortable and easy to maneuver. The bed was even better!! Will be a family destination from now on!

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
Thanks to David and his family for hosting us , it's a great place very clean and well put together everything was to our comfort, and meeting David and have a great conversation was the icing and the cake .Will definitely recommend it

Sunny guesthouse in coastal Maine
Extremely well-equipped (down to the Weber grill grates with the fold-up sides). Quiet, easy access to I-295, 15 minutes from Portland. Do note that plates and glasses are kept in rather tall cabinets, but I would very gladly stay here again.

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.

Fun and Sun Cozy Cabin-short walk to beach
When I first walked in, I sat on the couch and said to my husband, "perfect, this is perfect!" The location was in a very quiet neighborhood and close to the beach and the hot spots down by the pier in Old Orchard Beach. Everything was within walking distance. EVERY picture and description of the rental was spot on. The entire unit was very clean and had everything that we needed for the week we stayed. Communication with Anthony was great and instructions for checking in were very clear. We thoroughly enjoyed our week and were very comfortable.
Guest house rentals with a washing machine 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 !

Harraseeket Estuary Loft Apartment
What a lovely stay at Claire's Harasseeket Loft! It was quiet, warm and comfortable. I only stayed two nights but packed a lot in within those days as everything is a short distance away. Loved the shopping, eating, and meandering throughout Wolfe's Neck Wood State Park. Definitely do not miss that. But Claire's loft is in a beautiful location and well worth the stay. I would love to come back!

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
This is a wonderful space. Cleanliness, comfort, and privacy were unmatched. The listing is exactly as described and it is apparent the hosts take great pride in their home. Location was perfect; easy to access Portland, and a lovely historical local downtown. Would stay again without hesitation.

Close Enough - Beach Cottage
We would definitely like to stay here again. Easy to find, lots to do nearby and the cottage was super clean. Thanks again for thinking of everything…

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
Everything from cookware to furniture is high quality. Beautiful view right outside the door and very peaceful location. I would stay here again if I were in the area

Cozy 2BR retreat min toUSM&Sebago
Our stay at this Airbnb was truly exceptional. Joan and Andy are incredibly welcoming hosts who go above and beyond to make their guests feel at home. The property itself exceeded our expectations in every way—beautiful, comfortable, and thoughtfully maintained. We were more than satisfied with our experience and are already planning to make this our go-to spot for future trips. We genuinely can’t wait to come back. Rest assured, you'll be in great hands and can look forward to a relaxing and enjoyable stay. If I could give them more than five stars, I absolutely would.
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Attitash Mountain Resort
- Story Land
- Cranmore Mountain Resort
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Popham Beach State Park
- Brunswick Golf Club
- Long Sands Beach
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Palace Playland
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Mt. Abram
- Laudholm Beach
- Parsons Beach
- Things to do Cumberland County
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