Holiday Homes in Cumberland County

Sebago Lake House getaway

Relax with the whole family at this peaceful place to stay. Located 250 feet from beach entry lake. Relax on the dock or take the kayaks out for a spin. This charming house includes a mooring to keep a boat on. Located 30 min. From Portland, ME, 1 hour from North Conway, NH and 5 min. From Seacoast Adventures. Nearby hiking, swimming, breweries, and restaurants makes this house a great place to stay rain or shine. ** 7 night Saturday-Saturday rentals between June 27, 2026 - August 29, 2026**

Beautiful one bedroom cabin only 50 ft from beach4

This beautiful cabin features a queen bed in the bedroom, a double futon in the living room & can accommodate up to 4 people. The cottage includes a fully equipped kitchenette with microwave, mini-fridge, coffee maker, toaster & dining area. Smart TV, WIFI. AC & Central heating. A private full bath with tub/shower combo included at this unique and tranquil getaway. Enjoy the privacy of your own seaside cottage close to the beach! BBQ grills and picnic tables with umbrellas dot the outdoor area.

Lakehouse Paradise - A Slice Of Sebago Lake

Welcome to Sebago Lake! Come make memories at this charming lake house. The house is just a few minute walk from your private association beach on Sebago. Spend your days on the beach, in the crystal clear water, or out on the boat. Your warm Sebago nights can be spent BBQ'ing in the yard, roasting marshmallows at the fire pit, or playing card games inside. Enjoy the majestic views as the sun rises and sets over Maine's second largest lake. This is the perfect setting to make lifelong memories!

The Portland Getaway - 3 Bed Apt w Historic Charm

Newly renovated 3bd apt with historic charm and all the amenities to explore Portland's Restaurants, Arts, Coastline, Parks, and More! Located in the Oakdale Neighborhood the unit features 3 spacious bedrooms, 2 trendy bathrooms, beautiful eat in kitchen, cute office space, living room, off street parking and a large fenced in backyard with a fire pit. Walking distance to local attractions and 5-10 min drive to the Old Port and Waterfront. Come stay and enjoy all that Portland has to offer!

A Commanding View of Town of Old Orchard Beach

Distant Atlantic Ocean views from the lawn, deck, porch, or airy loft of this charming Old Orchard Beach rental. Perfectly located across from Walgreens for easy access to essentials. Both main bedrooms open directly outdoors to invite the fresh ocean breeze. Two additional converted sleeping areas, thoughtfully divided for privacy. Two showers and 4 parking spots. Explore “The Pier,” an iconic boardwalk, brimming with dining, and scenic charm. Your perfect coastal getaway awaits.

Walk to Beach + Eats | Dog&Family-Friendly Stay

Come stay in Pine Point! This cozy coastal escape is just steps to the beach for swimming, and the marsh for kayaking and close to seasonal restaurants. Perfect for multiple or extended families with a separate kid zone (beds, TV, games). Dogs will also love their stay with a fenced yard and great beach walks. The house is a quick trolley to Old Orchard Beach and 20 minutes to Portland’s airport, restaurants, and breweries. It also boasts a well stocked kitchen and an outdoor shower.

6-bedroom home with association lake & ATV trails

Perfect house for the outdoor lover! Sit outside by the fire pit at night and hear the owls and loons, watch the deer and other wildlife walk right by. Our 6 bedroom home is right on the ATV trails and a short walk to the private association lake with dock. The house can sleep up to 15 people comfortably. Great place to fish, hike and make great memories. The house comes full of outdoor games and rafts for the lake. It is a perfect house for large groups and families.

Bright and Spacious West End Charmer

This 3 BR/2BA apartment is located in the heart of Portland's historic West End neighborhood. Enjoy the use of the entire spacious, sunny first floor with your own private entrance, parking for 2 cars and private patio area (June-October). Located on a quiet street, but just steps away from modern conveniences and all that this great city has to offer: gourmet coffee shops, delicatessens, yoga studios, shopping, bars and dining, walking trails and the arts!

A Luxury Beach Stay near the beach!

Have fun at this stylish place. This unit is a 1-2 min. walk to a pristine Maine beach. Brand new renovation on entire apt. Yard space to relax in and your own grill to use. The kitchen is well stocked with cookware and the home feels comfortable and cozy. Full washer/dryer included. Parking on the premise available for 2 vehicles only. BR #1 - Queen, BR # 2,#3 two twins. Large kitchen. Excellent Wi-Fi. 4 additional units on the property for larger groups.

Coastal Modern Home By Woods, Near Portland

Our cozy guest house offers the best of all worlds. We have a rural, woodsy, secluded feel, but we're in close proximity to wonderful beaches, top restaurants, Portland, and other attractions by car, bike or jog. This cottage is situated on a five-acre, quiet, private, family-friendly property that backs up to the woods. The guest house itself is modern, spacious, open, and with many windows to the outside. We affirmatively welcome all. LGBTQ-friendly.

Heron's Perch on Peaks' Island

Heron's Perch on Peaks' Island has space to hold everyone and cozy spots to curl up on your own. Just steps to the market and ice cream shop and a short bike ride to the open ocean on the back shore. Beautiful porch to enjoy morning coffee and light filled rooms. Four bedrooms, two living rooms, back deck with grill and large lawn. We are in a residential neighborhood and for this reason the quiet hours are mandatory from 10PM-7AM.

House + Motor Boat. Waterfront. No Cleaning Fee.

House AND motor boat! Waterfront with fantastic view. No cleaning fees. Kids and pets friendly. Waterfront freshly renovated house in a quiet location, close to tourist destinations. Private dock and boat. Large deck, grill, fire pit. New bedding, full kitchen, new washer and dryer, huge TV, fast wifi, workstation. Perfect for a vacation and work from home. 5 min to the I-95.40 min to the Coast and Portland Pets welcome.