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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Harbor waterfront rentals
Waterfront apartment rentals
Apartment in Searsport
4.82 out of 5 average rating, 293 reviewsLakefront Vacation Apartment in Searsport ME
Feb 22 – Mar 1
Apartment in Tremont
5.0 out of 5 average rating, 129 reviewsDuck Cove Apartment
Apr 2 – 9
Apartment in Sedgwick
4.9 out of 5 average rating, 203 reviewsPrivate Apartment at Cabin Cove
Sep 24 – Oct 1
Apartment in Ellsworth
4.94 out of 5 average rating, 124 reviewsStill Point (where the river meets the sea)
May 31 – Jun 7
Apartment in Trenton
4.97 out of 5 average rating, 109 reviewsEco-friendly water view retreat near Acadia
Sep 27 – Oct 4
Apartment in Southwest Harbor
4.91 out of 5 average rating, 132 reviewsOn the water. Walk to Southwest Harbor
May 4 – 11
Apartment in Harrington
4.95 out of 5 average rating, 38 reviewsBeautiful Waterfront Home Close to Trails & Acadia
Apr 11 – 18
Apartment in Lamoine
4.93 out of 5 average rating, 68 reviewsRetro Retreat
May 6 – 13
Waterfront house rentals
Home in Eastbrook
5.0 out of 5 average rating, 110 reviewsThe Maine Getaway - Lakefront with Beach
Sep 7 – 14
Home in Trenton
4.93 out of 5 average rating, 242 reviewsAcadia National Park ocean front & garden cottages
Nov 8 – 15
Home in Stetson
4.96 out of 5 average rating, 151 reviewsLakefront Log Cabin on Pleasant Lake
Nov 26 – Dec 3
Home in Gouldsboro
4.92 out of 5 average rating, 26 reviewsAcadia’s Schoodic Oceanfront Cabin
Nov 4 – 11
Home in Winter Harbor
5.0 out of 5 average rating, 9 reviewsCaptain Guptill House views of Acadia & lighthouse
Oct 13 – 20
Home in Gouldsboro
4.96 out of 5 average rating, 48 reviewsEnchanting waterfront home on serene 15 acres
Nov 15 – 22
Home in Gouldsboro
4.9 out of 5 average rating, 21 reviewsBeautiful Oceanfront Estate
Feb 18 – 25
Home in Gouldsboro
5.0 out of 5 average rating, 19 reviewsMagnificent Oceanfront Modern, 8 Guests 4 Bedrooms
Jan 4 – 11
Waterfront condo rentals
Condo in Southwest Harbor
4.92 out of 5 average rating, 102 reviews2BR Condo w/ 3 min Walk to Downtown SWH [Low Tide]
Apr 8 – 15
Condo in Rockland
5.0 out of 5 average rating, 3 reviewsWaterfront Home! Rockland Harbor Views. STR23-25
Mar 7 – 14
Condo in Orland
4.98 out of 5 average rating, 40 reviewsToddy Haven: A Lakeside Condo Near Acadia.
Oct 24 – 31
Condo in Belfast
Harbor View Cottage - Cottage A
Jun 29 – Jul 6
Condo in Stonington
4.95 out of 5 average rating, 91 reviewsThe American Eagle - Inn on the Harbor
Jan 17 – 24
Condo in Southwest Harbor
4.91 out of 5 average rating, 85 reviewsMarina side Stern condo
Nov 25 – Dec 2
Condo in Southwest Harbor
5.0 out of 5 average rating, 9 reviewsBest views on MDI 2 bdrm 2 bth condo waterfront
Sep 7 – 14
Condo in Southwest Harbor
4.87 out of 5 average rating, 85 reviews2BR Condo w/ Ocean Views in Downtown SW [Seaglass]
Feb 18 – 25
Quick stats about waterfront rentals in Winter Harbor
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
960 reviews
Nightly prices starting at
$50 before taxes and fees
Destinations to explore
- Bar Harbor Vacation rentals
- Bangor Vacation rentals
- Acadia National Park Pond Vacation rentals
- St. Andrews Vacation rentals
- Camden Vacation rentals
- Grand Manan Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Halifax Vacation rentals
- Moncton Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Maine
- Waterfront rentals Maine
- Waterfront rentals Bar Harbor
- House rentals Winter Harbor
- Pet-friendly rentals Winter Harbor
- Family-friendly rentals Winter Harbor
- Rentals with a patio Winter Harbor
- Rentals with a fire pit Winter Harbor
- Rentals with a washer and dryer Winter Harbor
- Rentals with beach access Winter Harbor
- Monthly Rentals Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Rentals with a fireplace Winter Harbor
- Waterfront rentals Hancock County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes