Holiday houses in Winter Harbor

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Top-rated holiday rentals in Winter Harbor

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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.

26 Feb – 5 Mar

$334 NZD per night

Guest favourite

Home in Gouldsboro

4.94 out of 5 average rating, 118 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.

25 Oct – 1 Nov

$446 NZD per night

Guest favourite

Cabin in Eastbrook

4.95 out of 5 average rating, 184 reviews

Hemlock Cabin.

Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scamons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

16–23 Dec

$259 NZD 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.

2–9 Feb

$313 NZD per night

Guest favourite

Guesthouse 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 Dec

$213 NZD 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

$589 NZD per night

Guest favourite

Guest suite in Mount Desert

4.97 out of 5 average rating, 148 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.

2–9 Jan

$282 NZD 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

$242 NZD 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.

30 Sep – 7 Oct

$669 NZD 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 Feb – 7 Mar

$798 NZD 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!

28 Dec – 4 Jan

$287 NZD per night

Guest favourite

Cottage in Gouldsboro

5.0 out of 5 average rating, 163 reviews

Driftwood Cottage

This is the million dollar view on the Schoodic Peninsula. Sit on your private deck and private beach, sipping wine, while gazing across Frenchman Bay as the sun sets over Cadillac Mountain. Watch lobster boats crisscross the bay while eagles soar overhead.

20–27 Mar

$602 NZD per night