Holiday rentals in Winter Harbor

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winter Harbor

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Gouldsboro

4.93 out of 5 average rating, 188 reviews

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh water.

8–15 Feb

£159 per night

Guest favourite

Flat in Hancock

4.98 out of 5 average rating, 196 reviews

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.

8–15 Mar

£125 per night

Guest favourite

Home in Gouldsboro

4.94 out of 5 average rating, 117 reviews

Schoodic Loft Cabin "The Roost" with Kayaks

This playful cabin offers a unique spot to unwind and explore the Schoodic peninsula and Downeast Maine. Kayaks are provided to explore island studded 462 acre Jones pond, a 10 minute walk down a trail. A 10 minute drives brings you to the less visited Schoodic section of Acadia NP, where a network of hiking and biking trails lace the coastal forests and dramatic rocky coast. Nearby Winter Harbor has shops and restaurants and even a ferry across the bay to Bar Harbor and Mount Desert Island.

20–27 Oct

£215 per night

Guest favourite

Home in Winter Harbor

4.86 out of 5 average rating, 57 reviews

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! You'll never want to leave.

23–30 Aug

£268 per night

Guest favourite

Loft in Gouldsboro

5.0 out of 5 average rating, 29 reviews

Fisherman's Nook & Schoodic Retreat

Upstairs apartment, recently remodeled. Light filled. Open concept living room w/kitchen. Plenty of dishes, cooking, and bakeware. Living area: leather sofa with ottoman, recliner, smart TV, ceiling fan & window A/C. Bathroom: shower, vanity, flush, washer/dryer, laundry supplies, iron, toiletries, towels, blow dryer, and cleaning supplies. Bedroom: Queen platform bed, dresser, bedside tables, closet, ceiling fan, window A/C, and patio door onto small private deck w/stairs to ground level.

13–20 Oct

£167 per night

Guest favourite

Guest house in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

17–24 Mar

£94 per night

Guest favourite

Home in Winter Harbor

4.98 out of 5 average rating, 42 reviews

5 Mins to Acadia - Elegant Coastal Maine Retreat

Formerly owned by the founder of Burt's Bees, this 1900 colonial has been lovingly restored and updated. Every room has a designer's touch, filled with artistic furnishings, paintings and photographs, as well as, modern decor. Located in the heart of the historic Maine fishing village of Winter Harbor and only 5 minutes from the Schoodic section of Acadia National Park (1 hour to Bar Harbor) let this 3-bedroom, 2-bathroom house be your jumping off point for exploring all of Acadia.

19–26 Oct

£280 per night

Guest favourite

Guest suite in Mount Desert

4.97 out of 5 average rating, 147 reviews

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.

10–17 Nov

£134 per night

Guest favourite

Cabin in Winter Harbor

5.0 out of 5 average rating, 44 reviews

Schoodic Point Cabin

Warm and cozy vacation cabin built with your vacation in mind, a place having some illusion of being rustic and with all the comforts and conveniences of home. Pictures of the interior don't convey the ambiance inside. Especially in the evenings with the light from the fireplace reflecting off the vaulted ceiling. If you don't want to walk into a rental that looks like the house you just left. Then this may be the place for you!

2–9 Jun

£115 per night

Guest favourite

Home in Winter Harbor

4.86 out of 5 average rating, 155 reviews

Cozy Waterfront Cottage. Henry Cove, Winter Harbor

Right on the water — so close, it's like being on a boat — with great view of the harbor. Sit at the table, watching seagulls, bald eagles, the tide coming in and out — Downeast Maine at its best. 3 bedrooms, sleeps 5 (one room with a queen bed, one room with a double bed and one room with 2 twin beds), 1.5 baths.. A short walk to town. Guests return. The house is a comfortable family home, neat and clean, but not fancy.

28 Sept – 5 Oct

£318 per night

Guest favourite

Chalet in Gouldsboro

4.93 out of 5 average rating, 260 reviews

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

28 Dec – 4 Jan

£350 per night

Guest favourite

Home in Gouldsboro

4.94 out of 5 average rating, 123 reviews

The Adventure House

Our house was named “The Adventure House” by a family of houseguests with 3 fun and lively children. They told us that their time in Maine was filled with fun adventures so the kids started calling the house “The Adventure House” during their stay. We thought that was fitting as we are so close to Acadia National Park and many other pathways to adventures!

9–16 Dec

£125 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Harbor holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winter Harbor's top sights

Schoodic Point80 locals recommend

The Pickled Wrinkle74 locals recommend

Schoodic Woods Campground3 locals recommend

Chase's Restaurant20 locals recommend

Egg Rock Lighthouse3 locals recommend

Corea Wharf Gallery & Grill26 locals recommend

Other great holiday rentals in Winter Harbor

Guest favourite

Campervan/Motorhome in Gouldsboro

4.92 out of 5 average rating, 24 reviews

The Hummingbird

9–16 Nov

£94 per night

Guest favourite

Home in Gouldsboro

4.92 out of 5 average rating, 26 reviews

Acadia’s Schoodic Oceanfront Cabin

14–21 Nov

£272 per night

Guest favourite

Home in Winter Harbor

5.0 out of 5 average rating, 14 reviews

Winter Harbor's Hidden Gem

1–8 Feb

£321 per night

Guest favourite

Home in Winter Harbor

4.95 out of 5 average rating, 85 reviews

Anchor Down at Schoodic Point

23–30 Dec

£272 per night

Guest favourite

Home in Winter Harbor

5.0 out of 5 average rating, 9 reviews

Captain Guptill House views of Acadia & lighthouse

13–20 Oct

£286 per night

Guest favourite

Cottage in Gouldsboro

4.98 out of 5 average rating, 47 reviews

Stylish ocean-view home on Acadia's Schoodic Loop

18–25 Mar

£305 per night

Guest favourite

Home in Gouldsboro

4.89 out of 5 average rating, 47 reviews

Perfect 3 bedroom New England home.

28 May – 4 Jun

£218 per night

Superhost

Tiny home in Winter Harbor

4.91 out of 5 average rating, 11 reviews

Winter Hbr Oceanside Cabin - Schoodic Point (ANP)

30 Sept – 7 Oct

£195 per night

Show all

Quick stats about holiday rentals in Winter Harbor

Total rentals	90 properties
Rentals with dedicated workspaces	40 properties have a dedicated workspace
Pet-friendly rentals	20 properties allow pets
Family-friendly rentals	60 properties are a good fit for families
Total number of reviews	2.3K reviews
Nightly prices starting at	£40 before taxes and fees

Holiday rentals in Winter Harbor

Top-rated holiday rentals in Winter Harbor

Cottage in Gouldsboro

Flat in Hancock

Home in Gouldsboro

Home in Winter Harbor

Loft in Gouldsboro

Guest house in Orland

Home in Winter Harbor

Guest suite in Mount Desert

Cabin in Winter Harbor

Home in Winter Harbor

Chalet in Gouldsboro

Home in Gouldsboro

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winter Harbor holiday rentals

Stay near Winter Harbor's top sights

Other great holiday rentals in Winter Harbor

Campervan/Motorhome in Gouldsboro

Home in Gouldsboro

Home in Winter Harbor

Home in Winter Harbor

Home in Winter Harbor

Cottage in Gouldsboro

Home in Gouldsboro

Tiny home in Winter Harbor

Quick stats about holiday rentals in Winter Harbor

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore