Holiday rentals with breakfast in Cumberland

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

Family · Value · TV

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

Location · Value · Pets

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10 – 12. Large yard. Off street parking 6-8. Portland License #STHR-002587-2020

Location · Value · Backyard

Pet Friendly Audubon Bring Your Fishing Gear!

Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

Family · Value · Kitchen

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Family · Value · Getting around

Spacious, airy apt., steps from Eastern Promenade

Spacious and full of light, with everything you need for a comfortable stay. Keyless entry. Private deck. One bedroom with double bed. Fully updated bathroom with tub and shower. Fully updated kitchen. Large living area with Queen bed, sofa, and AC wall unit. Just steps from the beautiful Eastern Promenade and East End Beach which is great for swimming, paddling and kayaking. A quick walk to island ferries and The Old Port, markets, restaurants. License number: STHR-005953-2024

Family · Value · Nearby

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Location · Family · Hiking

Luxury Retreat In Back Cove | 10 Min to Downtown

Bike to downtown just 2 miles away. Ideal for a couple or family looking for a restorative getaway in a quiet, locals neighborhood. The architect owner designed and built this light-filled spacious eco-suite to meet the needs of the most discerning guest with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep soaking tub, fenced in backyard with deck, hammock, and pool - everything you need for a memorable Maine vacation!

Family · Location · Kitchen

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Family · Value · Sleep quality

The Nest! VERY CLEAN! Near downtown! Self check-in

**Please note: As of Summer 2026, Airbnb has shifted its service fee from guests to hosts. My rates & fees have been adjusted to reflect this change, not to increase my profit. The total ending cost to guests remains the same as before. :) Welcome to The Nest! We offer a beautiful private studio suite in Kennebunk, Maine! We are half a mile from downtown Kennebunk Village and less than 15 minutes to Kennebunkport and local beaches! A keyless entry makes check-in a breeze!

Family · Value · Decor

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Value · Location · TV

Glorious Converted 1865 Brunswick Barn in Town!

ANNOUNCEMENT: DURING SPRING SEMESTER (Jan-May) 2027 WE WILL GIVE A DRASTICALLY REDUCED "LOW SEASON" PRICE FOR 3-4 MONTH STAYS. 5 min walk from Bowdoin campus. Reach out and we're happy to work with you! "Brunswick Beata" is located steps from Bowdoin, restaurants, movies, public transportation & the town green. This colorful, unique and spotless gem is an extraordinarily comfortable and inspired place to stay while in Brunswick & surrounding area! Welcome!

Location · Family · Decor