Cottage
10.0(41 Reviews)
2 Bedrooms
5 Guests
Parking
Ocean View
Balcony/Terrace
View
CA $441/Night
7 Nights - CA $3,091
Winter Harbor Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Winter Harbor
10.0
House
10.0(1 Review)
3 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- View
Internet
CA $1,013/Night
7 Nights - CA $7,094
Apartment
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
CA $588/Night
7 Nights - CA $4,116
House
8.7(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $838/Night
7 Nights - CA $5,867
Apartment
10.0(7 Reviews)
1 Bedroom
4 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
CA $484/Night
7 Nights - CA $3,389
RV Rental
9.8(50 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $248/Night
7 Nights - CA $1,734
House
9.8(17 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $339/Night
7 Nights - CA $2,375
Cabin
9.8(16 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $407/Night
7 Nights - CA $2,849
Cottage
9.4(34 Reviews)
2 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $654/Night
7 Nights - CA $4,579
Luxury Holiday Rentals in Winter Harbor
Over 34+ Luxury Holiday Rentals in or Near Winter Harbor
House
10.0(27 Reviews)
7 Bedrooms
20 Guests
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
CA $4,361/Night
7 Nights - CA $30,527
House
10.0(32 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,628/Night
7 Nights - CA $11,393
House
10.0(4 Reviews)
5 Bedrooms
8 Guests
- Balcony/Terrace
- Kitchen
- Internet
Child Friendly
CA $1,552/Night
7 Nights - CA $10,865
House
9.8(18 Reviews)
3 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,070/Night
7 Nights - CA $7,493
Cottage
10.0(70 Reviews)
3 Bedrooms
6 Guests
- Ocean View
- View
- Kitchen
- Internet
CA $852/Night
7 Nights - CA $5,964
House
9.6(62 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $688/Night
7 Nights - CA $4,818
House
4 Bedrooms
8 Guests
- Parking
- Ocean View
- View
- Internet
CA $654/Night
7 Nights - CA $4,576
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Kitchen
- Internet
- Child Friendly
Laundry
CA $647/Night
7 Nights - CA $4,528
House
9.2(9 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $639/Night
7 Nights - CA $4,476
Pet-Friendly Holiday Rentals in Winter Harbor
Over 8+ Pet-Friendly Holiday Rentals in or Near Winter Harbor
House
10.0(26 Reviews)
3 Bedrooms
5 Guests
- Balcony/Terrace
- Kitchen
- Internet
Pet Friendly
CA $587/Night
7 Nights - CA $4,109
House
7.3(3 Reviews)
2 Bedrooms
7 Guests
- Parking
- Internet
- Pet Friendly
Security/Safety
CA $566/Night
7 Nights - CA $3,961
House
9.4(16 Reviews)
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $588/Night
7 Nights - CA $4,116
House
9.8(140 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $379/Night
7 Nights - CA $2,655
Condo
2 Bedrooms
5 Guests
- Parking
- Kitchen
- Internet
- Pet Friendly
CA $276/Night
7 Nights - CA $1,932
Apartment
10.0(48 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $591/Night
7 Nights - CA $4,137
Apartment
10.0(27 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $437/Night
7 Nights - CA $3,060
Apartment
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,139/Night
7 Nights - CA $7,969
Large Holiday Rentals and Private Villas in Winter Harbor
Over 3+ Large Holiday Rentals and Private Villas in or Near Winter Harbor
House
5.0(3 Reviews)
9 Bedrooms
24 Guests
- Balcony/Terrace
- Kitchen
- Child Friendly
- Laundry
CA $4,518/Night
7 Nights - CA $31,629
CA $476/Night
7 Nights - CA $3,331
House
4.7(3 Reviews)
3 Bedrooms
11 Guests
- Child Friendly
CA $330/Night
7 Nights - CA $2,313
Instantly Bookable Holiday Homes in Winter Harbor
Over 7+ Instantly Bookable Holiday Homes in or Near Winter Harbor
House
10.0(91 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $518/Night
7 Nights - CA $3,626
House
10.0(15 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $572/Night
7 Nights - CA $4,003
House
9.2(137 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $507/Night
7 Nights - CA $3,548
House
3 Bedrooms
7 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $586/Night
7 Nights - CA $4,102
Cottage
9.8(13 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $571/Night
7 Nights - CA $3,997
House
9.4(8 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $665/Night
7 Nights - CA $4,655
House
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Child Friendly
- Laundry
CA $459/Night
7 Nights - CA $3,212
Book a Last Minute Place to Stay in Winter Harbor
About Casai's Private Villas and Holiday Rentals in Winter Harbor
Discover more than 43 vacation rentals available in Winter Harbor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Harbor.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Harbor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Harbor. On average, places to stay near Winter Harbor offer 1249.15 ft², with nightly prices averaging CA $793.
With Casai, finding and comparing holiday rentals in Winter Harbor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Winter Harbor, ME
There are 43 Winter Harbor, ME Holiday Rentals
- Prices for a holiday home in Winter Harbor start at CA $248
- Top rated vacation home in Winter Harbor is Beautiful Victorian Cottage on Downeast Maine Coast ~ Next to Acadia Schoodic !
- Most popular short term in Winter Harbor is Schoodic Peninsula of Acadia Natl. Pk; ferry to Bar Harbor/Ocean - 15 Min. Walk
- Cheapest place to stay in Winter Harbor is Bold Coast Camp Minutes from Acadia's Schoodic Peninsula
- Most expensive holiday rental in Winter Harbor is One-of-kind estate with unique & luxurious decor and wooded oceanside location.
Recently Booked Holiday Rentals in Winter Harbor
- Lovely cottage on Acadia National Park's quiet Schoodic side. Pet friendly
- Prime Coastal Location! Large Family Villa
- Coastal View 2 bedroom Apartment with Private Balcony in Winter Harbor, Maine
- Charming Coastal House with Cozy Living Spaces and Outdoor Firepit
- Coastal View 1 Bedroom Apartment with Private Balcony in Winter Harbor, Maine
Frequently Asked Questions About Winter Harbor?
What are the top holiday rentals in Winter Harbor?
With numerous options available in Winter Harbor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Harbor:
- Beautiful Victorian Cottage on Downeast Maine Coast ~ Next to Acadia Schoodic !
- Acadia, Schoodic Peninsula, Frenchman's Bay Home, Henry's Cove
- Quaint and rustic cottage nestled on the shores of a small Maine village.
- Lovely cottage on Acadia National Park's quiet Schoodic side. Pet friendly
- Spectacular Oceanfront Home on Beautiful Maine Coast
- One-of-kind estate with unique & luxurious decor and wooded oceanside location.
- Guptill Cottage oceanfront with views of Acadia National Park
- Coastal View 2 bedroom Apartment with Private Balcony in Winter Harbor, Maine
- Downtown 3-Bedroom Home in Walkable Harborside Village
- Captain Guptill's House private beach, spectacular ocean views.
Which holiday homes in Winter Harbor are best for families?
If you're searching for a family-friendly holiday home in Winter Harbor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Harbor:
How many Casai.ca holiday rentals are available in Winter Harbor?
As of 2026, Casai boasts over 43 properties listed in the Winter Harbor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Harbor.
