House holiday rentals in Cumberland County

Explore Portland from a 18th-Century Victorian

*Covid-Clean* Cook breakfast in a bright kitchen with robust hardwood floors in this calm Victorian home. Sit down at a traditional dining table in an open-plan room featuring vivid wood-paneled walls, serene decor, and a geometric rug with pops of blue. Bright and spacious with entire top floor privacy. ** NO SHARED SPACE** This is a dedicated Airbnb apartment with no shared space whatsoever. Ultimate privacy. This apartment can be rented as (1) bedroom for up to (2) guests or as (2) bedroom for up to (4) guests. It is $50/night additional cost for the (2) bedroom. Please confirm the second bedroom is available if interested. Either option has a full bathroom with claw foot tub and shower. Full service kitchen with stove, refrigerator and microwave for your private use. Large living room with (2) couches and flat screen. The very large master bedroom with the ultra comfortable king size mattress also has cable tv. . Both the one bedroom and two bedroom option have their own private entrance, private kitchen and bath on the third floor. No shared space with anyone else with either the one or two bedroom rental options. Private entrance. Spacious one or two bedroom apartment with full kitchen, bath and living room as well as other amenities. We are available for any questions or concerns but as a rule we give the guests their privacy. The house is steps away from some of Portland’s most popular eateries including the Knotted Apron, Woodfords Bar and Grill, Bird and Co., The Treehouse, and Elsmere BBQ. Not far to the Old Port area to browse seafood markets and shops. Visit the Portland Observatory to explore a historic lighthouse. Close to all public transportation and Portland International Airport Parking in the driveway is a possibility, please ask if interested. Street parking is available, it is based on an odd /even system of the street address. You want to be parked on the same side as the date would be at 12:01 AM on any given day. You are staying at 32 Lawn Ave

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Waterfront 5 Bedroom Home Freeport 3 min to LLBean

Large, luxury 5 bedroom home set on 3.5 acres tucked away in the woods on Harraseeket Cove & South Freeport Harbor, great for kayaking & wildlife! WiFi, Smart TVs, backyard grills, firepit, outdoor furniture and kayaks. Waterfront tranquility just 3 minutes to Freeport's lively downtown shops, restaurants, breweries, and LLBean. Wolfes Neck State Park's stunning coastal trails and forests are close by and Portland's scenic Old Port is 20 minutes! Enjoy an authentic coastal Maine experience!

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

OOB Oasis - Spacious 5BR private Retreat w/ Pool

Welcome to our stunning home and your private oasis in Old Orchard Beach! Just 5 minutes from the ocean, this expansive custom-built retreat offers 3 suites (each with its own private bath), a gourmet kitchen with high-end appliances, a sprawling open floor plan, and ample parking for large groups. Step outside to enjoy a large fenced backyard, spacious deck with BBQ grill, and sparkling in-ground pool—perfect for summer fun, fall gatherings, or simply relaxing after a day at the beach.

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Modern & Sunny East End House. Private Parking!

This modern single-family home is just steps away from Portland's Eastern Promenade with its glorious views of Casco Bay and the islands. Many of the city's best restaurants, cafes, breweries & distilleries are all within a few blocks from the house. Park your car in the private parking spot behind the house and forget about it for a while and enjoy the city!