Holiday rentals with breakfast in South Portland

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Top-rated Holiday Accommodation with Breakfast in South Portland

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Top Guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 406 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

Top Guest favourite

Home in Portland

4.95 out of 5 average rating, 342 reviews

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

Guest favourite

Home in Portland

4.96 out of 5 average rating, 135 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew 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 eateries and breweries. 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Guest favourite

Apartment in Old Orchard Beach

4.96 out of 5 average rating, 78 reviews

Perfect Get-A-Way

Warm breezes, beautiful sunsets,the smell of the sea, sipping coffee on the porch, 2 minute walk to 7 miles of pristine beach, 10 minute walk to the Pier, restaurants, miniature golf, Palace Playland, shopping, train, Trolley, bus ... TAP ON PICTURE 2X TO READ THE CAPTIONS & FEEL THE EXPERIENCE OF OOB. Fireworks every Thursday. Private entrance. Off-street parking, bedding, towels, water, snacks, breakfast items, +amenities. Great for children 3yrs and up. May not appropriate for toddlers.

Top Guest favourite

Apartment in Portland

5 out of 5 average rating, 73 reviews

Luxe Eco Studio near Back Cove

2 miles from downtown, perfect for a couple or family looking for a restorative getaway. The owners, architect and landscaper, spent the last three years designing and building this light-filled spacious suite to meet the needs of the most discerning guest. Settle in with luxurious accommodations. Organic and down-topped king mattress, linen bedding, spacious marble rain shower, deep water soaking tub and heated slate floors are just a few amenities that will ensure a memorable Maine vacation!

Guest favourite

Home in Portland

4.92 out of 5 average rating, 249 reviews

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. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

Top Guest favourite

Apartment in Biddeford

4.98 out of 5 average rating, 140 reviews

Brenda and Phil's Place

Your rooms are isolated from the rest of the house on the second floor with a separate entrance that opens to a shared hall and laundry. The bedroom is large with an en suite bathroom and queen. The living room/ bunk room has two single beds, fridge, toaster, microwave. We have a wonderful, wooded location near Maine beaches and the University of New England. We are just minutes from Hills Beach and Fortunes Rocks Beach. Kennebunkport the city of Portland and Old Orchard beach are close.

Top Guest favourite

Home in Old Orchard Beach

5 out of 5 average rating, 22 reviews

Harper's Holiday 5 mins to beach!

Escape to relaxation in this cozy home, with Old Orchard's famous sandy beach dunes & pier just a 5-minute drive away! Enjoy peace & quiet while being close to all the entertainment & family fun. The spacious eat-in kitchen w/ cathedral ceilings is the perfect spot for entertaining & family meals. The private XL backyard is a tranquil oasis surrounded by gardens & trees. Host offers private boat tours as a bonus! Message for details. Your perfect Old Orchard Beach getaway awaits!

Guest favourite

Home in Limerick

4.93 out of 5 average rating, 127 reviews

Lakefront Getaway

Looking for a quiet peaceful getaway? Our Maine post and beam home is set on 7 acres of lake front. Great getaway to enjoy marshmallows and a roaring fire, kayaking, canoeing, swimming, boating or enjoy a great movie. For downhill skiers proximity to King Pine, Sunday River, Shawnee Peak and Black Mountain. Cross country and snow shoeing on property and on the lake. If you have a snow mobile- great trails available. Finally, great shopping in nearby North Conway at the outlets.

Top Guest favourite

Tiny home in Durham

4.99 out of 5 average rating, 352 reviews

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.

Guest favourite

Apartment in West End

4.8 out of 5 average rating, 275 reviews

Charming 1 Bedroom Flat in the Heart of Portland

Welcome to our stunning 1-bedroom apartment located in the vibrant and historic West End neighborhood of Portland, Maine! Nestled in a charming and tree-lined street... As you enter, you'll be greeted by an inviting living area bathed in natural light, thanks to the large windows. Relax on the sofa, enjoying a cup of coffee from the nearby local roasters, and plan your day's adventures using the complimentary high-speed Wi-Fi.

Superhost

Apartment in Scarborough

4.83 out of 5 average rating, 90 reviews

Seaside Escape – Walk to Beach, Trails & Food

Stay just steps from 7 miles of gorgeous sandy beach in this cozy Pine Point apartment. Enjoy peaceful vibes, walkable local eats like the Bait Shed, and easy access to Old Orchard Beach via the trolley. Close to Portland, the Eastern Trail, and more—perfect for a relaxing coastal getaway. Portland Jetport 20 min Eastern Trail 4 Minutes Ferry Beach State Park 12 Min Old Port in Portland 24 Min