
Vacation rentals with a pool in Cumberland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cumberland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cumberland rentals with a pool
House rentals with a pool

Love OOB! NEW 3 BR, 2.5 BA Maine Home
Heather’s place was by far the most well maintained and clean Airbnb our family has ever stayed in. She was responsive and kind with all our needs. The pool was conveniently located right across the road and a beautiful place to spend the warmer day. Walking to the OOB trolly, seafood restaurants and the best ice cream place we’ve visited yet. We look forward to making Heather’s place and a trip to the Maine coast an annual family vacation.

210 Sea Castle Circle
Very nice place, everything was clean and smelling good, we felt right at home! Comfortable beds except the single one which we could feel the springs. Expensive parking everywhere near the beach, be advised, but free parking at the house. Everyone at the place was friendly. The only thing mmissing would be coffee pods, for the rest, everything was there!

Lovely home with hot tub and pool
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!

Pool|HotTub|1Acr FencedYard|Firepit|Garden|PETS OK
Thank you for allowing us to stay at your beautiful home. The photos did it no justice! I can’t wait to be back, we will be stay here again.

The Lodge at Hidden Pines
The house was exactly as described and seen in the photos, a large, beautiful, authentic log cabin in the woods. The setting was quiet and beautiful though conviently right off the main road. We enjoyed cross country skiing, ice skating and a sleigh ride in Jackson (about 30 min away) and shopping in North Conway (about 20 min). Eileen made sure we were plowed and shoveled regularly during the snow storm so we enjoyed curling up by the fire and watching a movie on the large tv. My mother in particular enjoyed all the vintage decor which brought back childhood memories.

Walk to StoryLand!Updated Condo! WiFi/Golf/Pool/AC
Had a quick weekend getaway at Keith's place. Everything was perfect. Easy check in and great communication.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

There's No Place Like Home
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!
Condo rentals with a pool

White Mountains Hiking Dogs Storyland Family
Wife and I had a great time at Fairley’s place. Condo was as advertised, clean with all the utensils you need. The resort has a clubhouse with all great amenities. Location is great! We would definitely like to rent again.

Bartlett Condo; Great Views, Resort Access
This is the second time we have stayed at Bill's Condo. We love the location. I think this is one of the very best views in Nordic Village. Also, Bill is one of the best hosts that I have worked with. We had early check in which was great. The condo itself is very well stocked and had everything that we needed. Great Kitchen, comfortable bed, 2-person jet tub, and fireplace makes the condo very cozy and inviting. Hope to stay again soon.

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!

Generic Two Bedroom - Stair access only
The condo was very clean, tasteful decorated. Beds were comfortable. Loved the big table to play games and the living room was cozy for the evening and morning chats. Pretty views.

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!!!!

Peaceful Condo Near Storyland & Attitash Skiing
Very clean and relaxing place. Felt like home and will definitely visit back again. The host is very responsive and had clear instructions of everything.

Mountain views! Condo in amazing Nordic Village!
I stayed one night at Erics’ AirBnb with my girlfriend. It was amazing. Everything was very clean and it was exactly what the photos showed. The jacuzzi and views were definitely a highlight. It was 10 minutes away from Downtown North Conway which was really nice as well. Eric was very helpful and friendly, He responded to questions and comments very efficiently and was very caring. We had an amazing stay, I would 100% stay here again in the future. I highly recommend. Thank you!

Cozy Mountain Getaway For All Seasons
We had a great day! The place was perfect for our small group, and very convenient to the mountains for skiing. The condo had all the little things needed. And it was very comfortable. I would definitely book again.
Quick stats about vacation rentals with a pool in Cumberland
Total rentals
20 properties
Nightly prices starting at
$55 CAD 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
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Cranmore Mountain Resort
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Mt. Abram
- Dunegrass Golf Club
- Palace Playland
- Pemaquid Beach
- Laudholm Beach
- Parsons Beach
- Mothers Beach
- Middle Beach