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.

Point Sebago 2 bed 1.5 bath home. Sleeps 7

Peaceful 2 bed/1.5 bath home located in Point Sebago. Access to Sebago lake, golf and much more. Resort fee $10/day/per during peak season May-Oct. 1 king, twin over full bunkbed in 2nd bedroom and queen sofa bed. Linens not provided. Pillows provided. Fully equipped kitchen. Washer/Dryer. Weber Grill, stone fire pit. 18 hole golf course, restaurant, bar, snack bar, tiki bar, tennis, pickleball, shuffleboard, basketball, arcade, mini golf, playground, splash pad, entertainment. Marina too!

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!

Island View on Sebago Lake

Lakefront living is awaiting! Island View is a newly updated home that sits on 100 feet of sandy shore frontage on Sebago Lake. Spend your days on the lake, soaking up the sun on the private beach, fishing off the private dock, grilling with friends and family or relaxing on the expansive deck taking in the views. This 5-bedroom, 3.5 bath home with sleeping for 10 has a 1st floor master, updated appliances, granite countertops and is ideal for entertaining. You will never want to leave!

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.

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.

A Lovely 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.

Sebago Lakehouse: Hot Tub and Private Beach Access

Lovely 3 bedroom/2 bathroom house in the woods with a Hot Tub and access to the private shared beach! Sebago Lake is a perfect family destination for swimming, boating, and fishing. It is ideally located for a day trip to Portland, Old Orchard Beach, Kennebunkport, or Freeport. Or stay home, enjoy the Lake or watch the stars from the Hot Tub. Close to grocery stores and restaurants. Lake and beach access is only a 5-minute walk.

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, and parking for 2 cars. 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!