Waterfront vacation rentals in Winter Harbor

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Winter Harbor

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

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Guest favorite

Home in Jonesboro

4.96 out of 5 average rating, 104 reviews

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

Jun 2 – 9

R2,214 ZAR per night

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.

Mar 13 – 20

R3,270 ZAR per night

Guest favorite

Cabin in Steuben

4.96 out of 5 average rating, 163 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 :-(

Nov 2 – 9

R4,391 ZAR per night

Guest favorite

Cottage in Milbridge

4.97 out of 5 average rating, 166 reviews

Spring Waterfront Getaway! Hi-Speed Wi-Fi

GETAWAY 2024 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

Aug 27 – Sep 3

R6,208 ZAR per night

Guest favorite

Home in Hancock

4.98 out of 5 average rating, 127 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Apr 19 – 26

R6,553 ZAR per night

Guest favorite

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Apr 4 – 11

R2,645 ZAR per night

Guest favorite

Tiny home in Blue Hill

4.84 out of 5 average rating, 132 reviews

Mini Moose Tiny Home

Our Mini Moose sits on our 65 + acres of beautiful Maine woods. Two miles from the center of the coastal village of Blue Hill. Five years of rentals. Fire pit & view of the pond from the deck. 2 paths around 2 ponds, swimming is allowed and a contemplative walking labyrinth. Perfect getaway for a couple or single person to explore the natural beauty of Downeast Maine. Only 45 minute drive to Acadia National Park and close to all that Downeast Maine has to offer.

Sep 23 – 30

R1,860 ZAR per night

Guest favorite

Cabin in Sullivan

4.93 out of 5 average rating, 174 reviews

Private Waterfront Cabin off the Grid

Rustic, Simple, Picturesque cabin located onTaunton Bay & Schoodic National Scenic Byway. Only 25 miles to Acadia National Park & Bar Harbor. Watch the lobster boats & eagles from your front windows. Stay on the quiet side of Schoodic Acadia National Park, only 15 minutes away. Great for swimming & the kayak adventure. No electricity but battery lights. Close to Nature Preserves & Schoodic Mountain hiking trails. This cozy cabin has a lot to offer.

Apr 10 – 17

R1,747 ZAR per night

Guest favorite

Tiny home in Trenton

5.0 out of 5 average rating, 137 reviews

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Mar 23 – 30

R2,775 ZAR per night

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.

Dec 24 – 31

R6,147 ZAR per night

Guest favorite

Chalet in Gouldsboro

4.93 out of 5 average rating, 263 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

Apr 26 – May 3

R7,656 ZAR per night

Guest favorite

Cottage in Waltham

4.95 out of 5 average rating, 677 reviews

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

Apr 29 – May 6

R2,163 ZAR per night