Waterfront holiday rentals in Winter Harbor
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Top-rated waterfront rentals in Winter Harbor
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Winter Harbor
Waterfront apartment rentals
Flat in Tremont
5.0 out of 5 average rating, 129 reviewsDuck Cove Apartment
10–17 Dec
Flat in Searsport, Maine, US
4.82 out of 5 average rating, 293 reviewsLakefront Vacation Apartment in Searsport ME
1–8 Nov
Flat in Bayside, Canada
4.97 out of 5 average rating, 116 reviewsCharming Beachfront Apt w/Home Cinema & Coffee Bar
3–10 Apr
Flat in Sedgwick, Maine, US
4.9 out of 5 average rating, 204 reviewsPrivate Apartment at Cabin Cove
11–18 Sep
Flat in Trenton
4.97 out of 5 average rating, 110 reviewsEco-friendly water view retreat near Acadia
27 Sep – 4 Oct
Flat in Ellsworth
4.94 out of 5 average rating, 124 reviewsStill Point (where the river meets the sea)
4–11 Jun
Flat in Southwest Harbor
4.91 out of 5 average rating, 132 reviewsOn the water. Walk to Southwest Harbor
16–23 Nov
Flat in Harrington, Maine, US
4.95 out of 5 average rating, 38 reviewsBeautiful Waterfront Home Close to Trails & Acadia
15–22 Apr
Waterfront house rentals
Home in Eastbrook
5.0 out of 5 average rating, 110 reviewsThe Maine Getaway - Lakefront with Beach
25 Aug – 1 Sep
Home in Trenton, Maine, US
4.93 out of 5 average rating, 244 reviewsAcadia National Park ocean front & garden cottages
30 Oct – 6 Nov
Home in Stetson
4.96 out of 5 average rating, 151 reviewsLakefront Log Cabin on Pleasant Lake
6–13 Nov
Home in Gouldsboro
4.93 out of 5 average rating, 27 reviewsAcadia’s Schoodic Oceanfront Cabin
4–11 Nov
Home in Winter Harbor
5.0 out of 5 average rating, 9 reviewsCaptain Guptill House views of Acadia & lighthouse
13–20 Oct
Home in Gouldsboro
4.96 out of 5 average rating, 48 reviewsEnchanting waterfront home on serene 15 acres
1–8 Jun
Home in Gouldsboro
5.0 out of 5 average rating, 19 reviewsMagnificent Oceanfront Modern, 8 Guests 4 Bedrooms
30 Nov – 7 Dec
Home in Gouldsboro
5.0 out of 5 average rating, 9 reviewsCharming home on the quiet side of Acadia NP
24 Apr – 1 May
Waterfront apartment rentals
Apartment in Southwest Harbor
4.92 out of 5 average rating, 103 reviews2BR Condo w/ 3 min Walk to Downtown SWH [Low Tide]
28 Oct – 4 Nov
Apartment in Rockland
5.0 out of 5 average rating, 3 reviewsWaterfront Home! Rockland Harbor Views. STR23-25
4–11 Oct
Apartment in Orland
4.98 out of 5 average rating, 40 reviewsToddy Haven: A Lakeside Condo Near Acadia.
23–30 Oct
Apartment in Belfast
Harbor View Cottage - Cottage A
3–10 Dec
Apartment in Stonington
4.95 out of 5 average rating, 92 reviewsThe American Eagle - Inn on the Harbor
2–9 Dec
Apartment in Southwest Harbor
4.91 out of 5 average rating, 85 reviewsMarina side Stern condo
13–20 May
Apartment in Southwest Harbor
5.0 out of 5 average rating, 9 reviewsBest views on MDI 2 bdrm 2 bth condo waterfront
7–14 Sep
Apartment in Southwest Harbor, Maine, US
4.92 out of 5 average rating, 66 reviews2BR Condo Downtown SWH w/ Ocean Views [Driftwood]
5–12 Dec
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
€ 46 before taxes and fees
Destinations to explore
- Bar Harbor Holiday rentals
- Bangor Holiday rentals
- Acadia National Park Pond Holiday rentals
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- Rentals with a washing machine and dryer Winter Harbor
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