Guesthouse vacation rentals in Cumberland County

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Popular amenities for Cumberland County guesthouse rentals

Family-friendly guest house rentals

Guest favorite

Guesthouse in Scarborough

4.98 out of 5 average rating, 110 reviews

Smith Cottage Higgins Beach

MatthewRating, 5 stars1 month ago
Bev was a superb host! Met us when we arrived and all communication was prompt. Smith Cottage is lovely and super clean. Was perfect for visiting our son in Portland and enjoying Maine’s beauty together. Loved the sunrises on Higgin’s Beach!

Guesthouse in Brunswick

4.84 out of 5 average rating, 43 reviews

Stylish, high end, close to Bowdoin & town

ErikaRating, 5 stars77 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!

Guesthouse in Old Orchard Beach

4.85 out of 5 average rating, 27 reviews

1 Block to the Beach!

PatrickRating, 5 stars5 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 favorite

Private room in Poland

4.95 out of 5 average rating, 66 reviews

Stone's Throw from the Shore Bunk House

KenzieRating, 5 stars5 months ago
Judy’s camp was incredible and just what we needed to a getaway. Perfectly quiet and private location right on the water. Judy was very accommodating and quick to respond to any questions or messages we had to send to her! Very clean camp and looked exactly like the photos!! We hope to return again soon :)
Guest favorite

Private room in Cape Elizabeth

4.98 out of 5 average rating, 233 reviews

Salty Air in Cape Elizabeth | Portland | Beaches

ToniRating, 5 stars1 month ago
Sherry and John are just so lovely. They thought of everything. It was super clean and comfortable. They even left us with a little home crafted gift. If you’re a runner/walker, route 77 is very close and has a very wide shoulder both ways to safely exercise. Highly recommend Sherry and John’s cute little getaway.

Guesthouse in Old Orchard Beach

4.9 out of 5 average rating, 10 reviews

Location Location @ Tami Lyns Place

BritneyRating, 5 stars17 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!

Guesthouse in Hollis Center

4.86 out of 5 average rating, 59 reviews

Moment's Peace Farm Guest House

MaryRating, 5 stars63 months ago
Absolutely fantastic farm cottage with spectacularly beautiful surroundings. Joy and Peter made sure everything was perfect for our stay, and there wasn't a single thing we needed that wasn't provided. We enjoyed getting fresh eggs from the chickens in the mornings, picking fresh strawberries, lettuces, tomatoes, and more from the beautiful & abundant garden. The views from the cottage are like a postcard, and Joy and Peter made our stay comfortable, relaxing and fun. We stayed in the cottage for several months during both very hot and some chilly days and we were always comfortable. Enjoy your cocktails on the back deck while watching the rescue horses graze. You might even see some wild turkeys in the afternoons. If you want a peaceful place to stay near Portland, just like the name implies, A Moment's Peace Farm would be very hard to beat. Will definitely stay here again.

Guest house rentals with a patio

Superhost

Guesthouse in Westbrook

4.8 out of 5 average rating, 85 reviews

Modern stay Westbrook Maine

TenielRating, 5 stars1 month ago
Extremely clean and easy to access. The drive to Portland seemed quicker than expected so that was great. We enjoyed our stay!
Superhost

Guesthouse in Bridgton

4.88 out of 5 average rating, 107 reviews

Private apart with luxury view, mins to everything

HannahRating, 5 stars2 weeks ago
Gorgeous stay! Perfect for a romantic getaway to recharge. Beautiful space, pristine views of the snowy mountains. Cute nearby town with shops and restaurants. Linar was very helpful and responsive. Highly recommend!
Guest favorite

Guesthouse in South Portland

4.97 out of 5 average rating, 89 reviews

Willard Beach Guest House Minutes from Everything!

SheaRating, 5 stars2 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 favorite

Guesthouse in Westbrook

5 out of 5 average rating, 26 reviews

Riverfront guest house w/ patio

ChrisRating, 5 stars1 month 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 favorite

Guesthouse in Brunswick

4.96 out of 5 average rating, 116 reviews

Apartment in Brunswick with Country Charm No Fees

AlRating, 5 stars6 days ago
Good place to stay, vary cute and clean i recommend
Guest favorite

Guesthouse in Yarmouth

5 out of 5 average rating, 90 reviews

Sunny guesthouse in coastal Maine

DavidRating, 5 stars1 week ago
we enjoyed our stay and would stay again when we are in the area.
Guest favorite

Guesthouse in Brownfield

4.98 out of 5 average rating, 55 reviews

The Forested Bohemian . Tiny home/ tree house

MikhailRating, 5 stars2 months ago
Attention to detail is something we possess so it makes a difference staying in a place curated and managed by someone that does the same. It’s clear that Wanda has invested an abundance of time and love into her space. It’s also obvious that she has a gift to curate unique spaces. Her artist perspective is timelessly welcoming for anyone awake enough to notice her meticulous efforts. We’re so glad you’re sharing your gifts with the world Wanda. Thank you for opening your oasis to the public…your passion project is making a difference in the world!
Guest favorite

Guesthouse in Old Orchard Beach

5 out of 5 average rating, 14 reviews

Old Orchard Oasis

CassRating, 5 stars3 months ago
My partner, cat, and I had a wonderful stay at Nathan and Phoebe’s. The home was clean, comfortable, and charming. The cleanliness of the linens and towels especially stood out to me, and the hosts were extremely helpful and responsive. I was in Portland for a work trip that got extended, and they were super flexible. The home is also pet-proofed/friendly, so I had peace of mind knowing my mischievous kitten wouldn’t get into anything. All in all, awesome stay!

Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in West Bath

5 out of 5 average rating, 29 reviews

Spruce Ledge Boathouse

AshleyRating, 5 stars1 month 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 favorite

Guesthouse in Freeport

4.89 out of 5 average rating, 93 reviews

Harraseeket Estuary Loft Apartment

RoseRating, 5 stars1 month ago
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!

Guesthouse in Oxford

4.75 out of 5 average rating, 36 reviews

Camp in the woods in a luxury RV camper

JoyRating, 5 stars3 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 favorite

Guesthouse in Scarborough

5 out of 5 average rating, 8 reviews

Guest house, dead end Prouts Neck, Scarborough

LuciaRating, 5 stars2 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 favorite

Guesthouse in Yarmouth

4.99 out of 5 average rating, 127 reviews

Private Guesthouse in the Woods

WendyRating, 5 stars3 weeks 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 favorite

Guesthouse in Freeport

4.97 out of 5 average rating, 35 reviews

Downtown Freeport Barn’acle

EricRating, 5 stars2 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 favorite

Guesthouse in Gorham

5 out of 5 average rating, 37 reviews

Cozy 2BR retreat min toUSM&Sebago

AlisonRating, 5 stars2 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!
Guest favorite

Guesthouse in Bridgton

4.94 out of 5 average rating, 34 reviews

Bridgton Brick House Airbnb

Aubrey-LynneRating, 5 stars3 weeks ago
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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