Holiday Homes in Cumberland County

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Top-rated Holiday Homes in Cumberland County

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite

A serene lake scene is captured under a broad sky filled with clouds, reflecting shades of blue and gray. Gentle ripples disturb the calm water, while a wooden dock extends into the lake, offering a vantage point for outdoor enjoyment.

Holiday home in Windham

4.84 out of 5 average rating, 32 reviews

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**

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Superhost

Holiday home in Old Orchard Beach

4.72 out of 5 average rating, 230 reviews

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.

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Guest favourite

The exterior of the home features a charming two-story design with beige siding and dark blue shutters. A small porch is visible at the entrance, which is framed by a welcoming flag. Two outdoor chairs are positioned next to a round table, adding to the inviting atmosphere.

Holiday home in Casco

4.93 out of 5 average rating, 14 reviews

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!

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Guest favourite

A modern kitchen with sleek navy cabinetry and a farmhouse-style wooden table at the center. White stools are arranged around the table. Wall shelves display decorative items, and a large stainless-steel refrigerator is visible. Natural light enters through a window, enhancing the spacious feel.

Holiday home in Portland

4.93 out of 5 average rating, 163 reviews

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!

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Top Guest favourite

Holiday home in Scarborough

5.0 out of 5 average rating, 60 reviews

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.

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Guest favourite

The charming rental features a white exterior with a wraparound porch accented by hanging flower baskets. The lush green lawn surrounds the property, and large windows offer glimpses of natural light within. The sloped roof adds character to this welcoming structure.

Holiday home in Old Orchard Beach

4.89 out of 5 average rating, 37 reviews

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.

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Top Guest favourite

A bright living area features a gray sofa with colorful throw pillows, positioned across from a round wooden table. Three framed artworks adorn the white wall, while large windows allow natural light to fill the space. A patterned rug adds warmth to the wooden floor.

Holiday home in West End

4.91 out of 5 average rating, 138 reviews

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!

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Superhost

The kitchen area features modern cabinetry and stainless-steel appliances. A circular dining table, surrounded by four black chairs, is set with a decorative tray and a small plant, enhancing the functional space. Natural light streams through an adjacent doorway leading to another room.

Holiday home in Old Orchard Beach

4.82 out of 5 average rating, 100 reviews

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.

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The exterior of the guest house is displayed, featuring a white facade with large blue doors. The landscaped path leads to the entrance, bordered by colorful flowers and greenery. Tall trees surround the property, creating a serene atmosphere.

Holiday home in Cumberland

4.89 out of 5 average rating, 28 reviews

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.

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Guest favourite

A charming home is set in a green landscape, presenting a welcoming front porch with white railings and blue accents. Colorful flowering shrubs are positioned at the base of the porch, and a spacious lawn is showcased, providing a peaceful outdoor environment.

Holiday home in Peaks Island

4.95 out of 5 average rating, 40 reviews

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.

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Top Guest favourite

A spacious deck is shown, featuring a hot tub and a dining table surrounded by several chairs. An umbrella provides shade over the seating area, while comfortable outdoor furniture is arranged for relaxation. Lush green trees are visible in the background.

Holiday home in Windham

4.99 out of 5 average rating, 104 reviews

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.

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Guest favourite

A spacious living area features a large sectional couch, flanked by two side tables with lamps. A coffee table sits in the center, complemented by a small plant. Light filters in through two windows adorned with sheer curtains, enhancing the room's inviting ambiance.

Holiday home in Saco

5.0 out of 5 average rating, 23 reviews

Cozy Coastal 1 Bedroom Vacation Home!

Come relax at this cozy spot that has a pull-out couch that can sleep another two to three guests. Private entrance with parking for two cars and backyard with propane grill. Five minute walk to the restaurants downtown, five minute drive to the beach and walking trails, and 20 minutes from Portland. Dog are welcome, with a fee. Owner occupied duplex, we are available and happy to help make your stay more pleasant!!

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