Compare Winter Harbor Cottage Rentals

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Featured Cottages in Winter Harbor

Hanscom's Motel and Cottages

Hanscom's Motel and Cottages

3 out of 5
273 ME-3 Bar Harbor ME
$162 nightly
The price is $177 total per night
$177 total
May 25 - May 26
Total with taxes and fees
At Hanscom's Motel and Cottages, guests have access to free WiFi in public areas, express check-in, and express check-out. If you plan to drive, free parking is available. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include a terrace, barbecue grills, and a garden.
Pet friendly
Parking included
Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
318 Maine 3 Bar Harbor ME
$230 nightly
The price is $242 total per night
$242 total
May 19 - May 20
Total with taxes and fees
Guests of Hinckleys Dreamwood Cottages have access to free WiFi in public areas. If you drive, take advantage of free parking. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing.
Pet friendly
Parking included
Cozy cottage loft on the quiet side of Mount Desert Island -Now booking for 2026

Cozy cottage loft on the quiet side of Mount Desert Island -Now booking for 2026

Tremont ME
Guests staying at this cottage have access to a garden and barbecue grills. Staff members can answer questions about accommodations, and also provide concierge services.
Kitchen
Pet friendly
Wooded Cottage in Town walking to Marina, Restraunts

Wooded Cottage in Town walking to Marina, Restraunts

Southwest Harbor ME
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lakefront cottage near Acadia and Bar Harbor

Lakefront cottage near Acadia and Bar Harbor

Sullivan ME
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Bar Harbor Cottages & Suites

Bar Harbor Cottages & Suites

3.5 out of 5
144 Old Bar Harbor Rd Bar Harbor ME
Guests staying at Bar Harbor Cottages & Suites enjoy free WiFi in public areas, laundry facilities, and a garden. You can put free parking to good use if you drive. Helpful staff can provide dry cleaning/laundry services and concierge services. Additional amenities include barbecue grills and a picnic area.
Pet friendly
Parking included
Peaceful Cottage with Ocean Access

Peaceful Cottage with Ocean Access

Southwest Harbor ME
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Cozy Cottage in Bass Harbor, Maine next to Acadia National Park

Cozy Cottage in Bass Harbor, Maine next to Acadia National Park

Tremont ME
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Summer special! Adorable Whale's Tail guest cottage.

Summer special! Adorable Whale's Tail guest cottage.

Southwest Harbor ME
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Air conditioning
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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.

Hotel Options in Winter Harbor

    The Pathmaker Hotel

    The Pathmaker Hotel

    77 Cottage St Bar Harbor ME
    $149 nightly
    The price is $162 total per night from May 1 to May 2
    $162 total
    May 1 - May 2
    Total with taxes and fees
    9.8/10 Exceptional! (441 reviews)
    Bar Harbor Manor

    Bar Harbor Manor

    47 Holland Ave Bar Harbor ME
    $118 nightly
    The price is $129 total per night from May 3 to May 4
    $129 total
    May 3 - May 4
    Total with taxes and fees
    9.6/10 Exceptional! (1,001 reviews)
    Bar Harbor Grand Hotel

    Bar Harbor Grand Hotel

    269 Main Street Bar Harbor ME
    $199 nightly
    The price is $217 total per night from May 3 to May 4
    $217 total
    May 3 - May 4
    Total with taxes and fees
    9.8/10 Exceptional! (1,000 reviews)

Cottages

Book a cottage in Winter Harbor
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winter Harbor. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winter Harbor better.

Cottage apartments in Winter Harbor range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winter Harbor
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winter Harbor and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winter Harbor cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winter Harbor. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winter Harbor Cottages essential information

Accommodation
269 Cottages
Lowest Price
$129
Highest Price
$242
Popular accommodation
Hanscom's Motel and Cottages, Hinckleys Dreamwood Cottages, Cozy cottage loft on the quiet side of Mount Desert Island -Now booking for 2026, Wooded Cottage in Town walking to Marina, Restraunts, Lakefront cottage near Acadia and Bar Harbor, Bar Harbor Cottages & Suites, Peaceful Cottage with Ocean Access, Cozy Cottage in Bass Harbor, Maine next to Acadia National Park, Summer special! Adorable Whale's Tail guest cottage.