
Cottage holiday rentals in Winter Harbor
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Top-rated cottage rentals in Winter Harbor
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Edgewater Cabins #2
Edgewater is centrally located off of Route 1 (Schoodic Scenic By-way) in Sullivan Harbor. You can enjoy our beach and picnic tables on the wharf while surrounded by amazing views. You will find a tennis court just a short walk up our driveway. Nearby there are restaurants, local hiking trails, and Acadia National Park (20 min to Schoodic Point and 35 min to Acadia on Mount Desert Island). Boat rides around Frenchman's Bay are available from our dock. There's a 3 night minimum stay in Cabin 2.

Southwest Harbor Cottage
Enjoy unparalleled views of bustling Southwest Harbor and the beauty of Acadia National Park from the comfort of Eagle's Nest. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll into the village, where you'll find plenty of local shops and restaurants. You can access the water via a set of stairs leading from the property to the shoreline. End your days on the deck and keep your eyes peeled for seals!

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

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.

Cheerful 3-Bedroom Cottage moments from ocean
Mimi's Cottage is your getaway home located in the heart of Mount Desert Island. Acadia National Park is next door, as well as lighthouses, the ocean, and many outdoor activities for the whole family. We offer a welcoming rental experience for large and small groups. We are within moments of the ocean and our quaint little village of Southwest Harbor. Mimi's Cottage is thoughtfully furnished for young and old, and offers the perfect space for your Downeast Maine adventures.

Shore Haven - Oceanfront Home in Corea by the Sea
New gas fireplace insert of fall 2025** Peak season- Jun 14 to Sep 13, 2026- weekly bookings only with arrival/departure on Sunday***. This cedar shingled cottage home boasts 1850 sq ft of living space on one level. It has open concept Kitchen/Dining/Living/Sun room with spectacular ocean views; 3 bedrooms; 2 baths; and a library/reading room with a double bed. The property is nicely landscaped with a gently sloping lawn to 240 ft. of bold oceanfront.

Cozy Seal Harbor Cottage
We request anyone who stays on our property be fully vaccinated. Thank you for helping to keep our community healthy! This stand along cottage is on the same property as owner's home and includes 1 parking space. 2 bedrooms with full bath, laundry, and a fully stocked kitchen. House abuts Acadia National Park; Seal Harbor Beach and carriage roads are easy walking or biking distance! Only 12 minutes to Bar Harbor and 5 to Northeast Harbor.

11 Cute 1Br Acadia Cottage Open Hearth Inn
Cottage 11 is a quaint rustic cottage with one king bed, a full bath with shower, A/C, mini-fridge, cable, television, iron/ironing board, hairdryer, coffee pot, microwave, and free Wi-Fi. As with all guests who join our Ohana, there is full access to the indoor kitchen downstairs in the main building, the outdoor kitchen and grill, full access to the common use hot tub, and the bonfire pit on the back lawn.

Meadow Point Cottage
Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

320 Ft Of Private Beachfront w/ Stargaze Platform!
🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance! 🎅 Ho, Ho Ho...Tis The Season 🎅 Compass Point Cottage Will Be Decorated For The Holidays Through December!

Quiet lakefront cottage on Graham Lake
Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Cottage by Acadia National Park
Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.
Popular amenities for cottage rentals in Winter Harbor
Cottage rentals with a hot tub

Lakeview Cottage

Waterfront Great Pond Cottage w/ Hot Tub & Deck!

10 1BR Acadia Cottage w/AC Open Hearth Inn

Canoe House Bungalow and Spa Retreat ,Searsport

Beach cottage on Penobscot Bay

Nashport on the Penobscot

14 1Br Cottage in Bar Harbor Open Hearth Inn

Open Hearth Inn Cottage 12 - 10 min to Acadia!
Pet-friendly cottage rentals

Lake Front-Spa Tub-Fire Pit-Full Kitchen-Canoe

Stonington Harbor Cottage - Vacation / Remote Work

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Lakefront Cottage on Tracy Pond

Lakefront, near Bar Harbor, ME

Modern cottage with hummingbirds

Harbor views + stylish interior + boat lounge

Modern RV on Tracy Pond
Private cottage rentals

Cobblestone Beach Cottage

Harborside Comfortable Cottage! [Mermaid Cottage]

Camp Tranquility @ Rock Cove

Oceanfront Island: Hiker & Honeymooner’s Paradise

Private Waterfront Home with Kayaks and Firepit

My Blue Heaven

Salty Suite {Oceanside Cottage/Near Acadia}

Ledgewood Grove Cottage in Bar Harbor
Quick stats about cottage rentals in Winter Harbor

Total holiday rentals
Explore 10 holiday rentals in Winter Harbor

Nightly prices starting at
Winter Harbor holiday rentals start at £178 per night before taxes and fees

Verified guest reviews
Over 460 verified reviews to help you choose

Wifi availability
10 of Winter Harbor holiday rentals include wifi access

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

5 Average rating
Winter Harbor stays are highly rated by guests – averaging 5 out of 5!
Destinations to explore
- Rentals with a washing machine and dryer Winter Harbor
- House rentals Winter Harbor
- Rentals with a firepit Winter Harbor
- Rentals with a fireplace Winter Harbor
- Waterfront rentals Winter Harbor
- Pet-friendly rentals Winter Harbor
- Rentals with beach access Winter Harbor
- Family-friendly rentals Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Rentals with a patio Winter Harbor
- Cottage rentals Hancock County
- Cottage rentals Maine
- Cottage rentals United States
- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Sandy Point Beach
- Lighthouse Beach
- Sand Beach
- Bear Island Beach
- Spragues Beach
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Islesboro Town Beach
- Narrow Place Beach
- North Point Beach
- Billys Shore
- Three Island Beach
- Driftwood Beach
- Hero Beach
- Hunters Beach
- Gilley Beach
- Asper Beach
- Cellardoor Winery
- Bar Harbor Cellars
- Penobscot Valley Country Club
- Echo Lake Beach




