
Vacation rentals with a pool in Cumberland
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Top-rated rentals with a pool in Cumberland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Cumberland rentals with a pool
House rentals with a pool

Fantastic Kittery Home with Pool
The house was perfect for my family and I- plenty of open space for the kids to play and a great yard- even in December with cold weather the kids loved the play gym outside!! The location was amazing with lots of things to do within a few minutes and the food scene was great. Thanks to Ned for a spotless home and great amenities!! We can’t wait to come back in the summer to use the pool!!

Upscale OOB Beach House | Seasonal Heated Pool
Jason was a fantastic host—responsive, helpful, and easy to communicate with. Although we encountered a few minor issues during our stay, he responded immediately and went above and beyond to ensure everything was resolved quickly. The space itself was absolutely beautiful and made for a wonderful stay. I would highly recommend this place to anyone and hope to return in the future!

Fireplaced Mountain King Suite w/Hot Tubs & Pools
Great stay so homey and comfortable has everything we needed staying with two little girls ! Having laundry and kitchen made everything so convenient ! Close to so many things to do was the best vacation we’ve been on would definitely love to come back . Clean and organized everything was easy to find ! Great amenities pool ect !

Coolest Condo on the Lake!
We enjoyed our short, but lovely stay at the lake! Home was beautiful and warmly decorated. Comfy beds and set up so nicely! View of lake was so nice and it was hard to leave the deck. We loved the peace and quiet, relaxing vibe! Loved the closed in porch too! Enjoyed pickleball so easily accessible and pretty walk to the lakefront to relax. Wish we could have stayed longer, but rain made it easier to leave. We had magical weather our full day! We hope to return to this special area and home. Loved the market so close though! Thank you!!

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage
The house is beautiful and the views are just breathtaking. From inside the house, you get a beautiful view of the lake and then the porch is amazing. You can kayak, use the paddle board or use the canoe. You can also sit by the lake and enjoy the campfire. The surroundings are very beautiful and peaceful. The host is very responsive, solved all our doubts and was flexible with us during check-in and check-out, which we appreciated very much. At check-in, we were greeted by a great bottle of wine and chocolates, which was a great touch. The house also has a ping pong table, books to read and board games. The kitchen was well stocked with the basics. We had an amazing stay, we highly recommend this property :)

Lovely Beach house in GRB - Heated pool!
Great stay with our family of 6! Lots of space for everyone!

The Hill's on Buttonwood
Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

Pet Friendly Home, Ski Storage Room, HotTub, Sauna
This place was one of the best i’ve stayed in, and Joe & Colleen thought of everything you could possibly need to feel beyond comfortable. They were extremely kind and responsive hosts, and the space made us feel like royalty. What a fantastic experience, better than the pictures, we never wanted to leave the home. We enjoyed walking the neighborhood with our dogs, and did i mention the hosts left dog bowls, beds, toys, waste bags and more? This home is less than 10 mins from bethel village, 15 from sunday river, and 20 from beautiful grafton notch state park. Overall, the house was amazing, the sauna hot tub and heated pool were fantastic, and we would stay again in a heartbeat
Condo rentals with a pool

Attitash Studio | 5min to Storyland| Pools
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Across from Storyland & in the Heart of the Mtns
Beautiful place, has everything you might need. Very convenient location , close to storyland, restaurants and convenience stores . The restaurant recommendations from the host were great

KimBills’ on the Saco
We are a family of four and we stayed for four nights. It was larger than we expected and we were all quite comfortable. We loved that we could ski, swim, and have dinner without getting into our car on an extremely frigid (-17 degree windchill) day! It was a fun atmosphere and we loved our stay!

Cozy 1 BR Resort Condo; Fireplace; Amazing views
Great long weekend stay! Location perfect for trail/gravel biking, hiking, waterfall searching, and fly fishing! Perfect for 2…..great views to Doublehead and black mts. Accommodations were perfect. Kitchen stocked with essentials, large bathroom w separate jet tub…..and adequate hot water capacity to run it. Recommend highly.

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!

Cozy, clean, 2nd floor condo in Conway, NH!
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!

An Amazing Mountain Getaway!
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!
Quick stats about vacation rentals with a pool in Cumberland
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
320 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Laudholm Beach
- Ogunquit Playhouse