Photo by Simmie Reagor

Search Villas in Winter Harbor

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Villas in Winter Harbor

No exact matches found, but these alternatives could be just right

Recommended hotels in Winter Harbor

Exterior
One-of-kind estate with unique & luxurious decor and wooded oceanside location.

One-of-kind estate with unique & luxurious decor and wooded oceanside location.

Winter Harbor
10.0 out of 10, Exceptional, (25)
"The views are great and the host is pretty responsive too. Had an awesome time!"
United States
Calvin Ryan D.
The price is SAR 5,902
SAR 13,592 total
includes taxes & fees
12 Dec - 13 Dec
One-of-kind estate with unique & luxurious decor and wooded oceanside location.
Exterior
Coastal Red Farmhouse w/firepit, 5 BR, 8 beds, 1.5 BA, 6 acres, Narragaugus Bay.

Coastal Red Farmhouse w/firepit, 5 BR, 8 beds, 1.5 BA, 6 acres, Narragaugus Bay.

2.0 star property
Milbridge
The price is SAR 618
SAR 2,347 total
includes taxes & fees
4 Dec - 5 Dec
Coastal Red Farmhouse w/firepit, 5 BR, 8 beds, 1.5 BA, 6 acres, Narragaugus Bay.
Exterior
Downeast Maine Cottage with Water View and Nature Preserve

Downeast Maine Cottage with Water View and Nature Preserve

Steuben
10.0 out of 10, Exceptional, (15)
"We were in the area for a family reunion and we had a lovely time at this wonderful property. Everything is exactly as you anticipate!"
Canada
Jonathan H.
The price is SAR 503
SAR 1,629 total
includes taxes & fees
7 Dec - 8 Dec
Downeast Maine Cottage with Water View and Nature Preserve
Exterior
Cozy Milbridge retreat just steps away

Cozy Milbridge retreat just steps away

Milbridge
10.0 out of 10, Exceptional, (13)
"A very cozy place "
United States
Dylan J.
The price is SAR 591
SAR 972 total
includes taxes & fees
10 Dec - 11 Dec
Cozy Milbridge retreat just steps away
Property grounds
Sun Shed Farm Stay

Sun Shed Farm Stay

Milbridge
8.8 out of 10, Excellent, (6)
"We so appreciated the friendly, informative farm tour, as well as the option to purchase a farm breakfast, which was hearty and delicious. The animals were friendly. Truly a memorable experience."
United States
Richard
The price is SAR 255
SAR 360 total
includes taxes & fees
31 Dec - 1 January 2026
Sun Shed Farm Stay
Exterior
Corea Harbor Maine's Black Duck Inn - Downeast/Acadia - Victorian-era - July-Oct

Corea Harbor Maine's Black Duck Inn - Downeast/Acadia - Victorian-era - July-Oct

2.0 star property
Gouldsboro
The price is SAR 5,068
SAR 6,309 total
includes taxes & fees
31 Dec - 1 January 2026
Corea Harbor Maine's Black Duck Inn - Downeast/Acadia - Victorian-era - July-Oct
Exterior
Cozy cottage overlooking beautiful Bunker's Harbor in Birch Harbor, ME

Cozy cottage overlooking beautiful Bunker's Harbor in Birch Harbor, ME

Gouldsboro
9.6 out of 10, Exceptional, (8)
"Nice quiet beautiful location"
United States
Mary J.
The price is SAR 1,098
SAR 1,577 total
includes taxes & fees
14 Dec - 15 Dec
Cozy cottage overlooking beautiful Bunker's Harbor in Birch Harbor, ME
1 bedroom, WiFi, bed sheets
Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!

Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!

Gouldsboro
10.0 out of 10, Exceptional, (5)
"We loved the view of the harbor, the quietness of the area, and the adjacent restaurant (great coffee). The owner was very kind and our stay was lovely. "
United States
Lori
The price is SAR 676
SAR 949 total
includes taxes & fees
4 Dec - 5 Dec
Cozy studio with spectacular views of Bunker's Harbor in Birch Harbor!
Exterior
Water access house Acadia National Park Schoodic Point

Water access house Acadia National Park Schoodic Point

Gouldsboro
9.4 out of 10, Exceptional, (38)
"My family has an excellent time staying here for the week! There are tons of shops nearby, the host is very responsive, and the secluded nature of the home makes for a nice stay. We would definitely stay here again!"
United States
Addison Y.
The price is SAR 1,010
SAR 1,948 total
includes taxes & fees
4 Dec - 5 Dec
Water access house Acadia National Park Schoodic Point
Exterior
Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.

Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.

Gouldsboro
10.0 out of 10, Exceptional, (26)
"We had a great stay with our family of 4. We only stayed a few night but wouldn’t hesitate to return! "
United States
Darbey R.
The price is SAR 646
SAR 1,448 total
includes taxes & fees
4 Dec - 5 Dec
Private And Cozy Tiny Home For Your Acadia Escape. Pet Friendly with Kayaks.
Terrace/patio
Bluff House Inn

Bluff House Inn

3.0 star property
Gouldsboro
9.2 out of 10, Wonderful, (417)
"Very cozy place, great view, clean and quiet. "
United States
Igor
The price is SAR 158
SAR 377 total
includes taxes & fees
8 Dec - 9 Dec
Bluff House Inn
Exterior
Waterfront property on Frenchman’s Bay. Minutes from Acadia National Park & Downtown Bar Harbor. Newly furnished 3-bedroom, two baths with game room, outdoor grill and fire-pit.

Waterfront property on Frenchman’s Bay. Minutes from Acadia National Park & Downtown Bar Harbor. Newly furnished 3-bedroom, two baths with game room, outdoor grill and fire-pit.

2.0 star property
Bar Harbor
9.0 out of 10, Wonderful, (2)
"The host was wonderful. Great view and comfortable space ! "
United States
christine t.
The price is SAR 493
SAR 1,700 total
includes taxes & fees
4 Dec - 5 Dec
Waterfront property on Frenchman’s Bay. Minutes from Acadia National Park & Downtown Bar Harbor. Newly furnished 3-bedroom, two baths with game room, outdoor grill and fire-pit.
Exterior
Waterfront Cabin with private beach & unobstructed views of Frenchmen’s Bay. Just a few miles from Acadia National Park & Downtown Bar Harbor | Sleeps 6

Waterfront Cabin with private beach & unobstructed views of Frenchmen’s Bay. Just a few miles from Acadia National Park & Downtown Bar Harbor | Sleeps 6

2.0 star property
Bar Harbor
8.0 out of 10, Very Good, (2)
"Beautiful location on the ocean - still working on making it a perfect vrbo getaway, but I'm sure they will get there!"
United States
Fritz O.
The price is SAR 493
SAR 1,700 total
includes taxes & fees
4 Dec - 5 Dec
Waterfront Cabin with private beach & unobstructed views of Frenchmen’s Bay. Just a few miles from Acadia National Park & Downtown Bar Harbor | Sleeps 6
Fridge, microwave, oven, stovetop
Elegant Apt_Close to Downtown_Best Modern Features

Elegant Apt_Close to Downtown_Best Modern Features

Bar Harbor
9.2 out of 10, Wonderful, (19)
"Great place to stay, accommodating hosts and nearby downtown. "
United States
Srikanth S.
The price is SAR 926
SAR 1,793 total
includes taxes & fees
4 Dec - 5 Dec
Elegant Apt_Close to Downtown_Best Modern Features
Deluxe Apartment | Living area | Smart TV
Glen Mary Apartments

Glen Mary Apartments

3.5 star property
Bar Harbor
9.0 out of 10, Wonderful, (2)
"Fantastic "
United States
Amber
The price is SAR 1,072
SAR 1,731 total
includes taxes & fees
12 Dec - 13 Dec
Glen Mary Apartments
Sundeck
Acadia Hotel - Downtown

Acadia Hotel - Downtown

3.0 star property
Downtown Bar Harbor
9.2 out of 10, Wonderful, (987)
"Place was great!"
United States
Victor
The price is SAR 436
SAR 489 total
includes taxes & fees
8 Dec - 9 Dec
Acadia Hotel - Downtown
Fridge, microwave, oven, stovetop
Best Location & Best Free Breakfast! Newly Renovated 2bed/1bath, Heart of Downtown Bar Harbor

Best Location & Best Free Breakfast! Newly Renovated 2bed/1bath, Heart of Downtown Bar Harbor

Downtown Bar Harbor
9.8 out of 10, Exceptional, (51)
"Location was amazing! Apartment was well stocked and was perfect for 4 people. We enjoyed our stay!"
United States
Aimee H.
The price is SAR 1,773
SAR 2,831 total
includes taxes & fees
4 Dec - 5 Dec
Best Location & Best Free Breakfast! Newly Renovated 2bed/1bath, Heart of Downtown Bar Harbor
Exterior
The Sun Island Room - Lafayette Inn Bar Harbor

The Sun Island Room - Lafayette Inn Bar Harbor

Bar Harbor
8.8 out of 10, Excellent, (6)
"Perfect place near downtown. "
United States
Julia H.
The price is SAR 177
SAR 620 total
includes taxes & fees
4 Dec - 5 Dec
The Sun Island Room - Lafayette Inn Bar Harbor
Exterior
The Entire Lafayette Inn

The Entire Lafayette Inn

2.0 star property
Bar Harbor
The Entire Lafayette Inn
Exterior
Captain's Quarters in the Heart of Bar Harbor

Captain's Quarters in the Heart of Bar Harbor

Bar Harbor
10.0 out of 10, Exceptional, (4)
"A great location in walking distance to many dining options and all the shops as well as the waterfront. Parking situation was great and the set up inside was perfect. Very clean and well maintained. Highly recommend! "
United States
Sarah G.
The price is SAR 199
SAR 645 total
includes taxes & fees
7 Dec - 8 Dec
Captain's Quarters in the Heart of Bar Harbor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Harbor Hotel Reviews

Little Fig Hotel

Little Fig Hotel

10/10 Excellent
"This was a nice motel. The room was comfortable and very clean. They had a nice variety of muffins, yogurt, Kind bars, juice, coffee, teas, and hot chocolate in the mornings. In the evening there were home baked goodies. The staff was so friendly. I would definitely recommend this motel."
Elizabeth 3-night trip
Posted 2 days ago
Little Fig Hotel

Frequently asked questions

Why book your villa in Winter Harbor with Expedia?
With Expedia, it's easy to find your dream villa in Winter Harbor. Traveling with the kids? Use our helpful filters to search for stays with amenities like a pool and WiFi. If you're sticking to a budget, choose how much you're willing to spend and your preferred star rating. We'll help you find a perfect place that matches your taste and style.
How can I find cheap villas in Winter Harbor?
An excellent way to get cheap villas in Winter Harbor is with Expedia's useful filter tool. Fine-tune your search results by star rating, budget and amenities to nab awesome prices in only a couple of clicks.