House holiday rentals in Winter Harbor
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Top-rated house rentals in Winter Harbor
Guests agree: These houses 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 Winter Harbor house rentals
House rentals with a pool
Home in Bangor
4.96 out of 5 average rating, 225 reviewsCozy, fun, 3 bedroom home with a pool and Hot Tub.
8–15 Sep
Home in Bar Harbor
5.0 out of 5 average rating, 15 reviewsThe Haven at Hadley's
1–8 Aug
Home in Gouldsboro
4.75 out of 5 average rating, 4 reviewsThe ultimate Downeast compound w oceanfront pool!
7–14 Mar
Home in Surry
4.75 out of 5 average rating, 8 reviews3 Sisters Retreat, Newbury Neck, pool house
24–31 May
Home in Rockport
5.0 out of 5 average rating, 37 reviewsOcean View Retreat with Pool / Hot Tub
12–19 Mar
Home in Trenton
5.0 out of 5 average rating, 14 reviewsAcadia get away.! With pool and hot tub
5–12 Sep
Home in Ellsworth
5.0 out of 5 average rating, 60 reviewsThe Jarvis Homestead | Historic Maine Mansion
4–11 Apr
Home in Hancock
5.0 out of 5 average rating, 44 reviewsAnnabel’s Entire house . Pool.Firepit.Screen porch
10–17 May
Weekly house rentals
Home in Bar Harbor
4.99 out of 5 average rating, 171 reviewsHulls Cove Cottage
3–10 Dec
Home in Surry
4.89 out of 5 average rating, 168 reviewsPeaceful retreat on Newbury Neck
27 Sep – 4 Oct
Home in Mount Desert
4.88 out of 5 average rating, 155 reviewsParker Farm House
28 May – 4 Jun
Home in Bar Harbor
5.0 out of 5 average rating, 113 reviewsRenovated Bar Harbor Cottage just blocks from town
29 Mar – 5 Apr
Home in Mount Desert
4.96 out of 5 average rating, 201 reviewsIn the heart of Northeast Harbor & Acadia N. Park
17–24 Mar
Home in Bar Harbor
4.96 out of 5 average rating, 137 reviewsWalk to Everything DT Bar Harbor Mins 2 Acadia!
2–9 Sep
Home in Winter Harbor
4.98 out of 5 average rating, 42 reviews5 Mins to Acadia - Elegant Coastal Maine Retreat
20–27 Sep
Home in Winter Harbor
4.95 out of 5 average rating, 85 reviewsAnchor Down at Schoodic Point
19–26 Nov
Private house rentals
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
4.9 out of 5 average rating, 21 reviewsBeautiful Oceanfront Estate
17–24 Feb
Home in Gouldsboro
4.96 out of 5 average rating, 48 reviewsEnchanting waterfront home on serene 15 acres
9–16 Dec
Home in Gouldsboro
5.0 out of 5 average rating, 19 reviewsMagnificent Oceanfront Modern, 8 Guests 4 Bedrooms
4–11 Jan
Home in Gouldsboro
5.0 out of 5 average rating, 9 reviewsCharming home on the quiet side of Acadia NP
21–28 Dec
Home in Steuben
5.0 out of 5 average rating, 16 reviews3-bedroom 1798 Farmhouse
2–9 Jan
Home in Gouldsboro
5.0 out of 5 average rating, 7 reviewsSpruce Reach Shores
10–17 Nov
Home in Gouldsboro
4.89 out of 5 average rating, 27 reviewsWaterfront Coastal Retreat 4BR3BA w/ Private Cove
10–17 Mar
Quick stats about house rentals in Winter Harbor
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.3K reviews
Nightly prices starting at
$204 NZD before taxes and fees
Destinations to explore
- Bar Harbor Holiday rentals
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