Winter Harbor Vacation Rentals from $72: Search Short-Term Rentals

Q: What's the top vacation rental that Winter Harbor has to offer?

House near Acadia National Park : This vacation home rental outside Winter Harbor is located in a national park and offers a fireplace, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and an oven, so you can cook with friends or family.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winter Harbor vacation rentals

1. Quaint and rustic cottage nestled on the shores of a small Maine village.

Winter Harbor

Umesh K.

$886 nightly

Sep 7 - Sep 8

Total with taxes and fees

2. Stone Park

Ellsworth

Jennifer

$241 nightly

Sep 10 - Sep 11

Total with taxes and fees

3. Driftwood Cottage: Bass Harbor, ME

Tremont

Brandon

$514 nightly

Sep 23 - Sep 24

Total with taxes and fees

4. Moonshine a cozy studio apartment with views of Bunker's Harbor

Gouldsboro

Lori

$285 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. Cozy lodge minutes from Acadia National Park's Schoodic Loop!

Gouldsboro

$314 nightly

Sep 12 - Sep 13

Total with taxes and fees

6. Brand New House!! Charming tiny home close to Schoodic Peninsula.

Gouldsboro

$370 nightly

Sep 13 - Sep 14

Total with taxes and fees

Luxury Cabin, Hot Tub (Pets Not Allowed) | Exterior

7. Hinckleys Dreamwood Cottages

Bar Harbor

James

$236 nightly

Sep 7 - Sep 8

Total with taxes and fees

8. Hanscom's Motel and Cottages

Bar Harbor

Sarmila

$219 nightly

Oct 4 - Oct 5

Total with taxes and fees

City Apartment, 1 King Bed with Sofa bed, Kitchen | Living area

9. Downtown Apartments in Bar Harbor

Downtown Bar Harbor

Thuynga

$400 nightly

Sep 7 - Sep 8

Total with taxes and fees

10. Water access house Acadia National Park Schoodic Point

Gouldsboro

Linette

$546 nightly

Sep 7 - Sep 8

Total with taxes and fees

11. Bike, hike, kayak Acadia cottage

Gouldsboro

Natalie V.

$571 nightly

Oct 2 - Oct 3

Total with taxes and fees

12. Bar Harbor Condos

Bar Harbor

Joy

$325 nightly

Sep 7 - Sep 8

Total with taxes and fees

13. Downeast Maine Cottage with Water View

Steuben

Amanda R.

$442 nightly

Sep 8 - Sep 9

Total with taxes and fees

14. Private 14 acre waterfront 3-bedroom cabin in the peaceful forests of Maine

Gouldsboro

$399 nightly

Sep 30 - Oct 1

Total with taxes and fees

15. Isleview Gallery Rm 12 - 10 min to Acadia!

Trenton

Thomas Ethan G.

$176 nightly

Sep 12 - Sep 13

Total with taxes and fees

16. The Colonels Suites

Northeast Harbor

$340 nightly

Sep 18 - Sep 19

Total with taxes and fees

17. Bar Harbor Cabin Minutes to Downtown and Acadia National Park

Bar Harbor

Melissa C.

$439 nightly

Sep 9 - Sep 10

Total with taxes and fees

18. Cozy Milbridge Country Home

Milbridge

Gene B.

$257 nightly

Sep 5 - Sep 6

Total with taxes and fees

19. Sun Shed Farm Stay

Milbridge

Matthew

$101 nightly

Sep 5 - Sep 6

Total with taxes and fees

20. Oceanfront Cottage • Firepit + Beach • Near Acadia & Bar Harbor

Milbridge

Paul

$428 nightly

Sep 6 - Sep 7

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

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

The Pathmaker Hotel

10/10 Excellent

"Fabulous location and the attached free parking was a lifesaver. Very helpful front desk staff, who provided excellent fresh baked cookies and coffee. Restaurant was a disappointment, though. Free breakfast was included, but the food was mediocre at best. Coffee and fruit we're very good, however. It's stay again, just make other arrangements for meals."

Anchorage Motel

8/10 Good

"Convenient Location and Comfortable Beds, But Still Has a Motel Feel We arrived late in the evening and found that parking was limited. The front desk was very accommodating and helped us figure out parking in the check-in area, which we appreciated. The motel has been renovated, and the rooms are clean and updated, but it still has a definite “motel” feel. The beds were comfortable, which was a big plus after a long day. The bathroom was quite small and could use a little more space. I also would have appreciated a grab handle getting in and out of the shower, as well as more than two towels. The staff was accommodating when we requested an extra blanket, which was appreciated. Our room was not cleaned after the first night, although this seems to be pretty common at hotels these days unless you specifically request housekeeping. There aren't really any extra amenities, so don't expect a lot beyond the basics. That said, the location is excellent — it's within walking distance of downtown Bar Harbor, with restaurants and shops nearby, and only a few minutes from Acadia National Park. Overall, it's a good option if you're looking for a convenient, reasonably comfortable place to stay while exploring Bar Harbor and Acadia. Just keep your expectations in line with a renovated motel rather than a full-service hotel."

Find out more about Winter Harbor

Everything you need to know about Winter Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Harbor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Harbor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Harbor rentals

At Expedia, we put the best Winter Harbor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Harbor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Harbor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Harbor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Winter Harbor?

Yes, we have vacation rentals close to well known attractions in Winter Harbor, or you can go with a more remote option if you're looking for a relaxing stay. Winter Harbor is known for its waterfront and musical theater. Make sure you have time to check out the seafood restaurants and golf courses during your trip.

What's the top vacation rental that Winter Harbor has to offer?

House near Acadia National Park: This vacation home rental outside Winter Harbor is located in a national park and offers a fireplace, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and an oven, so you can cook with friends or family.

How many vacation rentals are there in Winter Harbor?

Expedia has 19 vacation rentals for your stay in Winter Harbor.

What’s there to see and do in Winter Harbor?

Acadia National Park and Schoodic Peninsula are a couple of lovely local spots to get outside and enjoy nature. Schoodic Point and Grindstone Neck Golf Course are other places to visit while you're in town.

What’s a vacation rental in Winter Harbor like?

Vacation rentals are private properties where you can stay for short or long periods in Winter Harbor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip.

Winter Harbor Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Winter Harbor vacation rentals

1. Quaint and rustic cottage nestled on the shores of a small Maine village.

2. Stone Park

3. Driftwood Cottage: Bass Harbor, ME

4. Moonshine a cozy studio apartment with views of Bunker's Harbor

5. Cozy lodge minutes from Acadia National Park's Schoodic Loop!

6. Brand New House!! Charming tiny home close to Schoodic Peninsula.

7. Hinckleys Dreamwood Cottages

8. Hanscom's Motel and Cottages

9. Downtown Apartments in Bar Harbor

10. Water access house Acadia National Park Schoodic Point

11. Bike, hike, kayak Acadia cottage

12. Bar Harbor Condos

13. Downeast Maine Cottage with Water View

14. Private 14 acre waterfront 3-bedroom cabin in the peaceful forests of Maine

15. Isleview Gallery Rm 12 - 10 min to Acadia!

16. The Colonels Suites

17. Bar Harbor Cabin Minutes to Downtown and Acadia National Park

18. Cozy Milbridge Country Home

19. Sun Shed Farm Stay

20. Oceanfront Cottage • Firepit + Beach • Near Acadia & Bar Harbor

Find vacation rentals that suit your style

Top Winter Harbor Hotel Reviews

The Pathmaker Hotel

Find out more about Winter Harbor

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app