Holiday rentals with a pool in Cumberland

Kennebunk/Kennebunkport Beach House w/Pool!

Perfect home for hosting and entertaining! Private in-ground pool, 600+ sq. ft. sprawling deck, large yard, and close proximity to beaches, restaurants, and shopping. Brand new renovations throughout! Amenities and features include: Newly renovated top to bottom 2 beautiful kitchens w/ granite, stainless steel appliances In-ground pool and 600 sq. ft. wrap-around deck Spacious 2 acre yard One mile from the beach Walking distance to Kennebunk Lower Village/Kennebunkport Dock Square Pet friendly!

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Welcome to your perfect White Mountain getaway! This spacious/pet friendly 2-bed, 2-bath condo offers 1200 sq ft just 1 mile from Attitash Mtn. Next to the clubhouse and nestled near the scenic Saco River, Storyland, Diana's Bath, and breathtaking hiking trails, it's an outdoor enthusiast's dream. Indoor heated pool, spa, game room, mini Fenway, and playground. Whether you're here to ski, hike, or simply relax, this condo is your ideal spot. Book instantly and receive 10% off on weekly rentals!

Cozy One bedroom condo near the beach with pool.

This cozy condo sleeps 4 people and located steps away from both Long Sands and Short Sans Beach. Newly renovated bathroom. The bedroom has a queen size bed and a barn door for privacy. The second bed is a queen size Murphy bed. The condo is equipped with everything you will need- linens, towels/beach towels, kitchenware, cook top, fridge, keurig, air fryer, microwave and toaster oven, beach chairs and grill. 7 night stay required. No Pets or AC. No smoking/vaping in unit. 2 parking spaces.

Attitash Family Apartment

Experience the perfect blend of space and comfort in our 4-bedroom, 2-bathroom apartment. Ideal for large groups and families, this property features three queen sleeper sofas for flexible sleeping arrangements. The open-concept living space boasts a fully equipped kitchen, dining area, and living room, fostering a communal atmosphere. 4 spacious bedrooms and two large bathrooms provide ample privacy. Guests also have exclusive access to our heated pool and direct access to the Saco River

Mountain Top Hidden Gem-1 King, Therapy Tub, Views

The true highest point of Nordic Village Resort with beautiful mountain views and peaceful surroundings. This is a spacious bedroom offers a king bed and a sitting area to enjoy the gas fireplace and get cozy for the evening. The balcony is great spot to look over the mountains, enjoy a sunrise & your morning coffee. Off the bedroom is a grand bathroom with jetted tub and shower. During the summer Chateau guests have access to a private pool and waterfall, just steps from the front door!

Cozy Family Retreat with Saco River Access

An ideal setting to enjoy Mt. Washington Valley's many year round outdoor activities or rest, relax and enjoy the peace. This cozy, comfortable condo has everything you and your guests might need to enjoy themselves. An upstairs, end unit with lots of natural light, and front and back decks. The inground pool is open in summer as are the tennis, shuffleboard and basketball courts. The common fields behind the condo are ideal for snowshoeing in the winter or walking in warm weather.

Entire Condo with pools close to Story Land/Skiing

Fun for the whole family! Unit sleeps 8 and is closest to the pools and hot tubs, and overlooks the pond where you can hang out by in the summer and skate in the winter. 2 minutes to Story Land, and multiple ski resorts within a 5-15 minute drive. (Black Mountain/Wildcat/Attitash/Cranmore and more!). Use the newly renovated kitchen with everything you need. This is our family’s condo- no parties. We want you to enjoy, but that won’t be tolerated.

Private Pool walking distance to Downtown Village

Come enjoy a fun and relaxing getaway at this centrally located home. We are the ONLY privately owned vacation home with a private in-ground pool within walking distance to the Village! Our home offers many different spaces indoor and outdoor to relax and build memories with friends and family. We hope you get out and enjoy all the area has to offer, while also feeling like you can return to unwind in our thoughtfully updated space.

Faith Lane with community pool

Newly built open concept with gorgeous quartz counters and vanities. 4 spacious bedrooms so large parties will be very comfortable. Deck with gas grill, table and chairs, and kids picnic table. Community pool and only minutes drive to the beach and pier. Located in the brand new Church Street Station community. The beach trolley stop is right at the entrance to the complex so makes for an easy quick ride to the beach.