
Guesthouse vacation rentals in Cumberland County
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Top-rated guesthouse rentals in Cumberland County
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Family-friendly guest house rentals

Smith Cottage Higgins Beach
We had another great week at Bev's cottage. This was our second time staying here. Perfect for our family of four. We love the walks to Higgins Beach (best beach in Maine!), to the market for great sandwiches, and we also ate at the Inn next door one evening for my wife's b-day. Bev is a very friendly host and can offer up expert local picks for anything you are looking to do. Can't wait to come back!

Stylish, high end, close to Bowdoin & town
We loved staying at Sarah’s place! It is so comfy and nicely designed. Sarah is super friendly and helpful. We had a fantastic experience. Highly recommended!

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.

Location Location @ Tami Lyns Place
This was the perfect spot for a long weekend with friends and kids! The beach is just steps away, and we loved being slightly removed from the busier area near the pier — it made for a more relaxing stay. The apartment was incredibly comfortable, and the thoughtful touches like free coffee, muffins, and cinnamon rolls were much appreciated. The hosts went above and beyond by providing brand-new sand toys for the kids, which was such a kind gesture. Having a store right downstairs made grabbing anything we needed super convenient. It was an absolute pleasure staying here!

Salty Air in Cape Elizabeth | Portland | Beaches
We had a great stay at this place. Check in instructions were provided in advance and overall a smooth process. The hosts provided us with water, snacks, coffee/tea options and had a written sign welcoming us which was all very thoughtful. The bed was comfortable and the bathroom was clean. It’s not too far from the central area for sightseeing. Overall we had a comfortable stay here so I highly recommend this place to anyone who is looking to visit Portland!

Queen bed suite; lake region!
Guest house rentals with a patio

North Coast Retreat | New Luxury Near Beaches
Leading up to my stay we started communicating to know everything I need to know for check in. Cindi was very flexible with the check in seeing I was on my motorcycle on a road trip and needed to get out the cold 🥶. Went inside and wow took my breath away. The home was perfectly laid out everything was there you needed. I would literally stay there forever lol. Very clean comfortable and just homey. I highly recommend this host and property 5 star rating all the way. Thank you Cindi for allowing us to stay in your home.

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!

Modern stay Westbrook Maine
Great, well-stocked place. Easy to get to downtown Portland. Worked good for four people. Responsive host.

Private Guesthouse in the Woods
We loved our stay here!! It was so clean, peaceful and comfortable. The surroundings were beautiful and the location was convenient to so many places. We highly recommend!!

Riverfront guest house w/ patio
Heather was a great host and made check in easy. Very cute place and perfect for two people. Would recommend staying here.

Discover Minglewood: A Peaceful Couple's Getaway
This location is nothing short of beautiful with plenty to do around Freeport and Portland. Kelly’s instructions were clear and we felt right at home during our visit

Sunny guesthouse in coastal Maine
Perfect location for attending a graduation in Portland! The space was bright, airy, and spacious—exactly what we were hoping for. We especially loved the cute design, well-equipped kitchen, and beautiful bathroom. Tucked in a quiet neighborhood, but still a quick and easy drive to Freeport & Portland.

Cozy Cabin Getaway-Walk to Beach & Fun!
This location is great. 10 minute walk to Old Orchard Beach Pier, beach & restaurants. Fairly quiet neighborhood. Cottage is big enough for 2 people.
Guest house rentals with a washer and dryer

Spruce Ledge Boathouse
We loved every minute we spent in this beautiful cabin. The views were stunning and the cabin was cozy. It's a truly delightful spot.

Harraseeket Estuary Loft Apartment
What a beautiful apartment nestled in the woods of Maine. Still close to the ocean and downtown Freeport. I was there in winter and it snowed. That made me appreciate the cozy comforter.

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.

Close Enough - Beach Cottage
Very clean and accommodating for all of our needs. We stayed here and drove to Bar Harbor one day. It was a bit of a drive but totally worth it to stay in Saco, near Portland as well.

Downtown Freeport Barn’acle
We had a great stay at the Barn'acle! Julia's home is located just a short walk from many great restaurants, cafes, and shops, as well as a quick drive from Wolfe's Neck Woods State Park and several other attractions. The space has recently been renovated and was very clean. We would love to stay there again next time we're in Freeport.

Private Hilltop View
Bernice is a sweet and wonderful host with a great sense of humor. This place made us feel like we had a home away from home and was even more special because it was in my hometown. There was everything needed to enjoy and maintain a great 5 nights in the natural surroundings of Maine. We also enjoyed meeting the young couple next door and there well mannered children. We surely hope that this property is available the next time that we head North.

Bridgton Brick House Airbnb
I can’t say enough great things about this location! It was so great to have the entire house, it was clean and beautiful. Felt so welcoming and I would recommend this house to anyone looking to be in town but also have privacy.
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Story Land
- Attitash Mountain Resort
- Long Beach
- Surfside Beach
- Popham Beach State Park
- Long Sands Beach
- Fox Ridge Golf Club
- Cranmore Mountain Resort
- Pemaquid Beach
- Brunswick Golf Club
- East End Beach
- Palace Playland
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Purity Spring Resort
- King Pine Ski Area
- Parsons Beach
- Ogunquit Playhouse
- Bald Peak Colony Club
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