House holiday rentals in Cumberland

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Popular amenities for Cumberland house rentals

House rentals with a pool

Guest favourite
Home in Sebago
5 out of 5 average rating, 18 reviews

Treehouse Farm - Sebago

HollyRating, 5 stars1 month ago
Great backyard with a pool, hot tub, fire pit and privacy with the woods.
Superhost
Home in Windham
5 out of 5 average rating, 5 reviews

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More

KimRating, 5 stars2 weeks ago
We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!
Guest favourite
Home in Biddeford
4.97 out of 5 average rating, 32 reviews

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK

Morgon-AshliRating, 5 stars1 week ago
Gorgeous house, peaceful area, a great back deck with pool and hot tub! Jey was a great host, very helpful and quick response time. The house was very clean and put together. I would totally recommend staying at jeys house!!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars8 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Guest favourite
Home in Bartlett
4.81 out of 5 average rating, 121 reviews

Walk to StoryLand!Updated Condo! WiFi/Golf/Pool/AC

SHAUNRating, 5 stars4 months ago
Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.
Guest favourite
Home in Portland
4.95 out of 5 average rating, 127 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

IrmaRating, 5 stars3 weeks ago
Angela’s place was wonderful! Very cozy, clean and comfortable, well stocked, close to downtown Portland. Snacks was a nice touch! Angela was very responsive. Hope to come back soon!
Guest favourite
Home in Portland
4.82 out of 5 average rating, 110 reviews

There's No Place Like Home

JeremyRating, 5 stars8 months ago
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!
Top Guest favourite
Home in Scarborough
5 out of 5 average rating, 14 reviews

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches

Lisa-MarieRating, 5 stars1 week ago
Top notch spot and host!! We had such a great time at Alexa’s lovely home! It was so cozy, beautifully decorated, modernized, and had all the essential items you’d need - plus it is completely pet friendly! Our dog loved the fenced in yard with a doggy door to get out to it. The sauna, endless pool, and hot tub are just amazing amenities to have on site - that sunroom was my favorite place in the house to say the least! Can’t say enough about it and Alexa, too! She is super friendly, responsive, and had great recommendations for fun and good food in the area. Overall, it was just a wonderful and relaxing experience for our first time on the Maine coast and we can’t wait to visit again!

Weekly house rentals

Top Guest favourite
Home in Falmouth
5 out of 5 average rating, 28 reviews

Charming Coastal Home

AbigailRating, 5 stars1 day ago
Kelsey was a great host, super responsive and allowed us to check in earlier due travel changes. The home was well-stocked with everything we needed for a ten-day stay and very clean upon arrival. Location is great; central to both small town and urban charm. Would definitely stay again!
Top Guest favourite
Home in Windham
5 out of 5 average rating, 31 reviews

Maine Vacation Home on the Water

SamRating, 5 stars6 days ago
Kate’s place is in a beautiful location and has so much to do. We loved the wildlife, the easy access to Portland and all the yard games. We can’t wait to come back!
Guest favourite
Home in Portland
4.83 out of 5 average rating, 53 reviews

Cute Craftsman Bungalow home w/ fenced in yard

NicoleRating, 5 stars2 weeks ago
Kevin's place worked really well for my two dogs and myself. There is a fenced in back yard. I liked the setup of the primary bedroom with the attached full bath and laundry. Comfortable bed! Very quiet neighborhood and very convenient to access other areas of Portland. I really appreciated the back deck setup. I need to find the comfy chair they have out back for my own home! Clean and usable kitchen. Nice stack of Maine materials and recommendations for local items to check out. Overall, a very pleasant stay, thank you!
Superhost
Home in Falmouth
4.89 out of 5 average rating, 9 reviews

Oceanfront Home in Falmouth

JosephRating, 5 stars20 months ago
Beautiful, well-appointed home. All the little things add up to a stress-free experience. Fully stocked with towels, cooking supplies, even q-tips if you forget your own! By far the cleanest, most comfortable AirBNB I've stayed in. Photos don't do justice to the view from inside and from the patio. Incredibly quiet at night and the feeling of seclusion helped recharge my batteries. Super clear directions and entry instructions. Nothing beats dinner or wine by the firepit overlooking the bay except for the sunrise over the water. Would 100% stay again.
Superhost
Home in Falmouth
4.95 out of 5 average rating, 76 reviews

Wild Rose Farm -Three Queen Suites

RongshiRating, 5 stars2 weeks ago
My friends and I had a great time staying at this Airbnb. The host was very responsive and made everything easy for us. Our favorite part of the stay was definitely the barn. It was spacious, cozy, and perfect for hanging out and playing games. Highly recommend!
Superhost
Home in Windham
4.7 out of 5 average rating, 67 reviews

The "Happy Hen House" cottage in lakes region

MattRating, 5 stars8 months ago
As Mainer living across the country, it is always nice to come. Unfortunately this trip was to attend my Mom's funeral. Pam's home was the right level of closeness to the rest of my family to make visiting easy. The place was the peaceful retreat I needed to visit with myself. Five minutes to most things a person living out of a suitcase could need. Also less then 5 minutes walk puts one at the boat launch for personal watercraft. A great place to sit for a few. The amenities were plentiful at the house and the character was Maine charming. Pam was wonderful and easy to communicate with at all stages. I will be back in the future. Matt
Guest favourite
Home in Georgetown
4.96 out of 5 average rating, 23 reviews

Breathtaking Bay Views!

ColletteRating, 5 stars8 months ago
I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.
Top Guest favourite
Home in Windham
4.98 out of 5 average rating, 46 reviews

Modern Chic Home in Windham

ChristineRating, 5 stars2 months ago
Here’s anCarley's home was wonderfully equipped with all the essential amenities to make my stay comfortable. I particularly appreciated the thoughtful touches like coffee (with filters!) and a well-stocked kitchen, which made the space feel warm and homey rather than like a typical hotel. During my visit, it snowed, and Carley had everything I needed to stay safe, including a shovel and rock salt to keep the steps clear. The extra blankets were a cozy bonus that I truly appreciated on chilly nights. The home is situated in a quiet, charming neighborhood with convenient access to nearby stores, making it an ideal home base for visiting family in the area. Highly recommend!

Private house rentals

Top Guest favourite
Home in Biddeford
5 out of 5 average rating, 5 reviews

Bluebell Cottage Beach Vacation

KeithRating, 5 stars1 week ago
Would definitely stay here again. Was really a first class space that made our family feel very relaxed.
Top Guest favourite
Home in Freeport
5 out of 5 average rating, 47 reviews

Waterfront Cottage in Freeport

BrianRating, 5 stars2 weeks ago
Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!
Guest favourite
Home in Freeport
4.9 out of 5 average rating, 94 reviews

Spacious Country Home, 5 min to LL Bean Freeport

AnnmarieRating, 5 stars1 month ago
Fantastic stay! Comfortable, peaceful and amazing location. Lots of space we felt right at home and our dog loved going for walks in the yard. We look forward to staying again!
Superhost
Home in Freeport
4.8 out of 5 average rating, 35 reviews

Amazing location! Cheerful home near LL Bean

EmilyRating, 5 stars8 months ago
Such a lovely, cozy spot! We stayed for two nights with toddlers and our dog and everyone was very happy there.
Guest favourite
Home in Gray
4.97 out of 5 average rating, 33 reviews

Little Sebago Lakefront Getaway

DanielRating, 5 stars8 months ago
Violeta and her space were amazing. The house was exactly as advertised and we felt right at home for our long weekend. We are looking forward to making this a yearly visit!
Top Guest favourite
Home in Portland
5 out of 5 average rating, 57 reviews

Convenient Portland home 3 miles from Downtown

NancyRating, 5 stars1 week ago
We really enjoyed our stay at this Air Bnb. We have stayed at over twenty different locations with Air Bnb and this was the cleanest. Beds were comfortable, space was open and uncluttered. It was nice to be able to have dinner on the back deck. We would definitely stay here again.
Superhost
Home in Windham
5 out of 5 average rating, 5 reviews

Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs

CheriRating, 5 starstoday
Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.
Top Guest favourite
Home in Windham
5 out of 5 average rating, 14 reviews

Woodland with Fireplace Home

MarloRating, 5 stars3 weeks ago
We rented this beautiful home while attending our daughter's graduation from UNE. This home provided us with plenty of space for our family and had everything you would need to make your stay enjoyable. The beds were very comfortable, and the towels and linens were top quality. We felt the home was close to everything we needed. We wished the weather was a little better for us; we would have liked to enjoy the outdoor deck! Don't pass on renting this home. It's a 10+! Thank you for sharing your home with us.

Quick stats about house rentals in Cumberland

  • Total rentals

    90 properties

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore

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