Holiday Homes in Cumberland County

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Top-rated Holiday Homes in Cumberland County

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Guest favourite
Holiday home in Old Orchard Beach
4.71 out of 5 average rating, 207 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.

Superhost
A sandy beach leads to a wooden dock extending over clear waters. Several boats can be seen moored nearby, with distant hills appearing under a bright blue sky. The scene captures a tranquil lakeside setting perfect for relaxation.
Holiday home in Standish
4.8 out of 5 average rating, 40 reviews

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!

Top Guest favourite
An outdoor seating area is set within a well-kept yard, featuring a mix of patio chairs and lounge seating around a fire pit. A large wooden table sits adjacent to the house, shaded by an umbrella. Tall trees and hedges provide privacy, enhancing the inviting outdoor space.
Holiday home in Scarborough
5 out of 5 average rating, 54 reviews

Point Paratus Pine Point; Kid, Dog & EV Friendly

Come visit Pine Point! This beach house is steps away from the ocean for swimming, marsh for kayaking, and many seasonal restaurants. It is an ideal vacation location; set up well for multiple families with a separate "kid zone" complete with beds, tv and games. Dogs will also want to tag along to enjoy the fenced in yard and morning beach walks. Short trolley to Old Orchard Beach and a 20 minute drive to Portland’s airport, restaurants, and breweries. Fully stocked kitchen & outdoor shower.

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
4.91 out of 5 average rating, 137 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!

Superhost
A lakefront home is positioned amid trees with a sandy shore in the foreground. The two-story structure features large windows and a welcoming front porch. A private dock extends into the water, providing access for outdoor activities.
Holiday home in Sebago
4.87 out of 5 average rating, 15 reviews

Sebago Lake Waterfront Home w/ Sandy Beach & Dock

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!

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
4.9 out of 5 average rating, 31 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.

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 Portland
4.9 out of 5 average rating, 120 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!

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
4.85 out of 5 average rating, 89 reviews

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.

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
4.88 out of 5 average rating, 24 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.

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, 83 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.

Guest favourite
A spacious outdoor deck is seen featuring a wooden floor, a round table, and several striped chairs. A large blue umbrella provides shade over the seating area. A small propane grill is positioned nearby, surrounded by lush greenery and trees.
Holiday home in Harrison
4.94 out of 5 average rating, 31 reviews

Private Apartment Steps to Crystal Lake with Deck

Bright, sunny second floor apartment one block from Crystal Lake Beach on a quiet street right in Harrison Village. Enjoy sunsets on your private deck, walk two blocks into town, or three blocks to Long Lake Park. Perfect for a couple or solo traveler and the (new) pullout sofa can accommodate a third. Beautiful back deck with southern and western exposure. Full kitchen, small propane grill, TV & high speed internet.

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
4.81 out of 5 average rating, 27 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.

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