Winter Harbor vacation rentals

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Top-rated vacation rentals in Winter Harbor

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

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Guest favorite

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.

Guest favorite

Farm stay in Franklin

4.91 out of 5 average rating, 504 reviews

Boreal Blueberry Bungalow - Organic Farm Getaway

This sweet bungalow is located on a tucked-away organic farm, 45 minutes from Bar Harbor and Acadia National Park, and directly abutting the Downeast Sunrise Trail and thousands of acres of conservation land. Newly crafted space with pine interior and cork flooring. For folks who appreciate simple living but want a cozy bed! Cot available for third person. Full size mattress, all bedding, stove with oven, pots, pans and dishes, small fridge and sawdust based composting toilet (on back porch)

Guest favorite

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.

Guest favorite

Cabin in Steuben

4.96 out of 5 average rating, 162 reviews

*Stunning Views* Oceanfront Chalet

Oceanfront cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Jun 15- Oct 15 Friday-Friday weekly rental. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Guest favorite

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.

Guest favorite

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!

Guest favorite

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.

Guest favorite

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.

Guest favorite

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

Guest favorite

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!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winter Harbor vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Winter Harbor

Guest favorite

Cottage in Gouldsboro

4.89 out of 5 average rating, 123 reviews

Shore Haven - Oceanfront Home in Corea by the Sea

Guest favorite

Cottage in Waltham

4.95 out of 5 average rating, 673 reviews

Quiet lakefront cottage on Graham Lake

Guest favorite

Cottage in Roque Bluffs

4.97 out of 5 average rating, 171 reviews

Ellie's Cottage—lovely, bright, and tasteful

Guest favorite

Cottage in Blue Hill

4.88 out of 5 average rating, 190 reviews

Brand new cottage close to downtown Blue Hill

Guest favorite

Cottage in Hancock

4.99 out of 5 average rating, 317 reviews

Lillebo

Guest favorite

Cottage in Lamoine

4.95 out of 5 average rating, 244 reviews

Lamoine Modern Guest House

Guest favorite

Cottage in Mount Desert

4.97 out of 5 average rating, 171 reviews

Craney "Tree" House near Acadia

Guest favorite

Cottage in Sullivan

4.94 out of 5 average rating, 106 reviews

Edgewater Cabins

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Other great vacation rentals in Winter Harbor

Guest favorite

Apartment in Hancock

4.98 out of 5 average rating, 196 reviews

Flower Farm Loft

Guest favorite

Tiny home in Trenton

5.0 out of 5 average rating, 134 reviews

The Tiny House with the Enormous View of Acadia

Guest favorite

Cabin in Winter Harbor

5.0 out of 5 average rating, 44 reviews

Schoodic Point Cabin

Guest favorite

Loft in Gouldsboro

5.0 out of 5 average rating, 29 reviews

Fisherman's Nook & Schoodic Retreat

Guest favorite

Home in Winter Harbor

4.98 out of 5 average rating, 42 reviews

5 Mins to Acadia - Elegant Coastal Maine Retreat

Guest favorite

Home in Winter Harbor

4.86 out of 5 average rating, 59 reviews

Cozy & Walkable Winter Harbor Home next to Acadia

Guest favorite

Camper/RV in Gouldsboro

4.92 out of 5 average rating, 24 reviews

The Hummingbird

Guest favorite

Home in Gouldsboro

4.92 out of 5 average rating, 26 reviews

Acadia’s Schoodic Oceanfront Cabin

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Quick stats about vacation 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
$50 before taxes and fees

Frequently Asked Questions

What types of vacation rentals are available in Winter Harbor?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Winter Harbor. From over 10 cottage rentals to over 40 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there pet-friendly vacation rentals in Winter Harbor?
Four-legged friends are welcome in Winter Harbor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winter Harbor?
Yes! Work meets play with ease at over 40 vacation rentals in Winter Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cottage rentals in Winter Harbor?
Experience the best of Winter Harbor with our cottage rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Winter Harbor have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Winter Harbor have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Winter Harbor?
Winter Harbor has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winter Harbor have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.

Winter Harbor vacation rentals

Top-rated vacation rentals in Winter Harbor

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Winter Harbor vacation rentals

Stay near Winter Harbor's top sights

Other great vacation rentals in Winter Harbor

Cottage in Gouldsboro

Cottage in Waltham

Cottage in Roque Bluffs

Cottage in Blue Hill

Cottage in Hancock

Cottage in Lamoine

Cottage in Mount Desert

Cottage in Sullivan

Other great vacation rentals in Winter Harbor

Apartment in Hancock

Tiny home in Trenton

Cabin in Winter Harbor

Loft in Gouldsboro

Home in Winter Harbor

Home in Winter Harbor

Camper/RV in Gouldsboro

Home in Gouldsboro

Quick stats about vacation rentals in Winter Harbor

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What types of vacation rentals are available in Winter Harbor?

Are there pet-friendly vacation rentals in Winter Harbor?

Are there vacation rentals with a dedicated workspace in Winter Harbor?

How much does it cost to stay in cottage rentals in Winter Harbor?

Do cottage rentals in Winter Harbor have wifi?

Do cottage rentals in Winter Harbor have air conditioning?

Are there family-friendly cottage rentals in Winter Harbor?

Do house rentals in Winter Harbor have a bbq area?

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