
Holiday rentals with outdoor seating in Winter Harbor
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Winter Harbor
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Maine Country Home Young
Take it easy at this unique and tranquil getaway. This little country home sits in town in the fishing village of Winter Harbor, Maine. Explore Schoodic Point, a part of Acadia National Park, while hiking, fishing, bicycling, kayaking, and picnicking at Frazer Point.Several area restaurants are within walking distance and serve up Maine traditional fare.Want to enjoy Bar Harbor as well? Take the ferry from the marina and experience sea life such as dolphins, seals, or a bald eagle on your trip.

Flower Farm Loft
When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

The Adventure House
The Adventure House was named by a family of houseguests with 3 fun and lively children who filled their time here with adventures at Acadia National Park and beyond! We are 10 minutes from the quiet side of the park and just under an hour to the busy side, both filled with scenic beauty! We have an added amenity for families traveling with extra family or friends. We're now offering a beautiful camper that comfortably sleeps 6 on the property available only for an extra charge after booking.

Whitetail by the River, Acadia National Park 10m
Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Cozy & Walkable Winter Harbor Home next to Acadia
Walk everywhere in Winter Harbor while enjoying picturesque Downeast Maine right next to the most peaceful section of Acadia National Park on the Schoodic Peninsula. This vintage cottage has everything you need to relax in a quintessential fishing village. Walk to coffee shops, restaurants, bars, a grocery store, the Bar Harbor Ferry and gorgeous harbor views. Avoid the traffic and congestion of Bar Harbor and come experience Downeast Maine's best kept secret! Sorry no dogs allowed.

Lamoine Modern Guest House
Relax, recharge, & escape here. A unique & peaceful guest house in the woods of Lamoine, Maine with large windows looking out to the woods. Close enough to Bar Harbor / Acadia National Park (45 minutes) but removed from the hustle & bustle. A 10-minute walk down a gravel road to a beach in Lamoine with distant views of Acadia National Park. Enjoy all weather with our new wood stove fireplace surrounded by large windows. We have a comprehensive guidebook for our guests upon check-in.

The Acadia House on Westwood
Relax with the whole family at this tranquil centrally located place to stay. Slowly unwind at this lovingly remodeled entire home. Enjoy a peaceful walk down the quiet family friendly street its nestled on, or quickly arrive at all the areas attractions. The house is located in Ellsworth Maine and although shops, restaurants, local lakes, Acadia National Park and area attractions are only a quick drive away, the home feels soothing, very safe, secluded and welcoming to all.

Otter Creek Retreat hosted by Elaine & Richard
Between Bar Harbor and Seal Harbor, 10 minutes by car to both and just 5 minutes by car to the Otter Cliff entrance to Acadia Park Loop Road. Walk to the Causeway via the Grover Path in 15 minutes. 5-minute walk to the Cadillac South Ridge Trail. Large high-ceiling studio with private parking and entrance with beautiful sheltered second-story deck. We are on the Blackwoods/Bar Harbor bus route so you can catch the free Island Explorer LL Bean buses to Bar Harbor and back.

2BR Condo Downtown SWH + Ocean Views [Driftwood]
This newly renovated 4th Floor Condo was completed in 2022. Enjoy a private deck and your view of Southwest Harbor! The open concept design of the main living space of the home is great for groups to enjoy together! **In 2023 we switched from Window A/C Units to Portable A/C Units to reduce noise from road in bedrooms** Location Highlights: -4min Drive to Bass Harbor -18min Drive to Acadia National Park [Hulls Cove Entrance] -20min Drive to Downtown Bar Harbor

Private Downtown Bar Harbor Studio
Charming cabin-inspired efficiency apartment on a quiet side street in the heart of downtown Bar Harbor. Just a stone's throw (literally) from Main St and a minute walk down the street to the ocean and Bar Harbor's famous Shore Path. High speed wifi, SmartTV with Netflix provided (HBO, Hulu, Amazon, etc. are available to use with your own account), washer/dryer, large closet, hair dryer, assorted supplies, Bose bluetooth player, and snacks.

Great Timbers Retreat Minutes from Schoodic Park
This private newly renovated log home is nestled right next to the ocean front. Radiant floors with all new appliances and granite countertops. Spa showers in both bathrooms. One large bedroom with king bed and two Queen luxury futon beds for guest. Stone fireplace. Brand new washer and dryer. Charcoal grill outside and picnic table with ocean views. Pet Friendly there are pet beds and crate available

Anchor Down at Schoodic Point
Anchor Down in this nautically inspired salt box home in the quaint seaside town of Winter Harbor, Maine. Comfortably furnished and well equipped for your vacation getaway. At Anchor Down you will be conveniently located across the road from the entrance to Acadia National Park's Schoodic Penninsula with hiking and biking trails and gorgeous views of the ocean.
Popular amenities for outdoor seating rentals in Winter Harbor
House rentals with outdoor seating

[Trending Now]Sail Loft

Coveside Lakehouse on Sandy Point

Bayview House 1br 2ba Stunning Harbor Views

Renovated Bar Harbor Cottage just blocks from town

Water's Edge-Oceanfront with Stellar View

The Boathouse on the ocean

Hulls Cove Cottage

The Arthaus, an eclectic retreat for two
Apartment rentals with outdoor seating

Acadia Adventures

Clean and cozy studio

Coastal, relaxing, light-filled + walkable

Duck Cove Apartment

Echo Woods Loft with view of Acadia Mountain

Sunny In-Town Camden Studio, 10% weekly discount

Stepanec Castle

Lakeside Studio with hot tub, kayaks and canoe
Apartment rentals with outdoor seating

BLUE HILL Village Condo - Great In-Town Location

Acadia Village Resort 1 Bedroom Manor

Two-bedroom condo near Acadia National Park, Maine

Marina side Stern condo

16 Apartment near Acadia Open Hearth Inn

Modern Condo #3!

Toddy Haven: A Lakeside Condo Near Acadia.

Best views on MDI 2 bdrm 2 bth condo waterfront
When is the best time to visit Winter Harbor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $252 SGD | $285 SGD | $252 SGD | $258 SGD | $299 SGD | $322 SGD | $410 SGD | $412 SGD | $374 SGD | $362 SGD | $317 SGD | $298 SGD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals with outdoor seating in Winter Harbor

Total holiday rentals
Explore 70 holiday rentals in Winter Harbor

Nightly prices starting at
Winter Harbor holiday rentals start at $127 SGD per night before taxes and fees

Verified guest reviews
Over 3,350 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Winter Harbor holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Harbor rentals

4.9 Average rating
Winter Harbor stays are highly rated by guests – averaging 4.9 out of 5!
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