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Baileys Harbor Holiday Rentals

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Our top choices for Baileys Harbor holiday rentals

1. Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
Baileys Harbor
10.0 out of 10, Exceptional, (116 reviews)
"Amazing find! Beautiful place, well kept and has all the touches of home. The host was a great communicator and helpful! Definitely would recommend this place to a friend!"
United States
Crystal G.
The price is NZ$919
includes taxes & fees
10 Nov - 11 Nov
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

2. Landmark Resort

Landmark Resort
3.5 star property
Egg Harbor
9.0 out of 10, Wonderful, (710 reviews)
"Beautiful property with spacious rooms and the staff helped me during my stay."
United States
Romaine
The price is NZ$347
includes taxes & fees
6 Dec - 7 Dec
Landmark Resort

3. Scandinavian Lodge

Scandinavian Lodge
3.5 star property
Sister Bay
9.4 out of 10, Exceptional, (1,730 reviews)
"Wonderful staff and very clean resort!"
United States
Shannon
The price is NZ$237
includes taxes & fees
11 Nov - 12 Nov
Scandinavian Lodge

4. Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (82 reviews)
"Good location, good hotel. "
United States
shane
The price is NZ$281
includes taxes & fees
10 Nov - 11 Nov
Evergreen Hill Condominiums

5. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (530 reviews)
"Great place to stay-beautiful location with great amenities"
United States
Megan
The price is NZ$381
includes taxes & fees
10 Nov - 11 Nov
Waterbury Inn

6. Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi

Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
Fish Creek
9.6 out of 10, Exceptional, (85 reviews)
"Great place, clean, great location!"
United States
Lynn M.
The price is NZ$283
includes taxes & fees
10 Nov - 11 Nov
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi

7. Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (990 reviews)
"Great location and awesome staff to make your stay fun and relaxing."
United States
Matthew
The price is NZ$223
includes taxes & fees
15 Nov - 16 Nov
Westwood Shores Waterfront Resort

8. Private 3BR Gem on 2.5 Wooded Acres- Close to All

Private 3BR Gem on 2.5 Wooded Acres- Close to All
Sister Bay
10.0 out of 10, Exceptional, (61 reviews)
"Fantastic property - was perfect for our family of 5."
United States
Andrew L.
The price is NZ$890
includes taxes & fees
10 Nov - 11 Nov
Private 3BR Gem on 2.5 Wooded Acres- Close to All

9. CONDO 3-Sister Bay Serenity-Luxurious downtown condo!

CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
Sister Bay
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful condo located perfectly in the downtown of Sister Bay."
United States
John H.
The price is NZ$747
includes taxes & fees
11 Nov - 12 Nov
CONDO 3-Sister Bay Serenity-Luxurious downtown condo!

10. Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (706 reviews)
"Very nice stay."
United States
Brenda
The price is NZ$302
includes taxes & fees
10 Nov - 11 Nov
Bridgeport Waterfront Resort

11. Jacksonport Woodland Hearth Retreat - Near Lake Michigan

Jacksonport Woodland Hearth Retreat - Near Lake Michigan
Sturgeon Bay
10.0 out of 10, Exceptional, (8 reviews)
"What a fantastic way to enjoy Door Co! This VRBO really made our stay perfect! Beautiful home in a lovely part of the peninsula with all the amenities - nearby Lake MI beach, tranquil woods, and great restaurants. This host and home couldn’t have made our stay more relaxing!"
United States
Michelle T.
The price is NZ$764
includes taxes & fees
10 Nov - 11 Nov
Jacksonport Woodland Hearth Retreat - Near Lake Michigan

12. Harbor View Penthouse Downtown Egg Harbor

Harbor View Penthouse Downtown Egg Harbor
Egg Harbor
10.0 out of 10, Exceptional, (4 reviews)
"All was wonderful! Beautiful property, perfect location."
United States
Beth D.
The price is NZ$1,330
includes taxes & fees
10 Nov - 11 Nov
Harbor View Penthouse Downtown Egg Harbor

13. THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
Ephraim
9.8 out of 10, Exceptional, (98 reviews)
"Super cozy cottage just a short drive from town. Adorable courtyard with great landscaping. A perfect getaway for my mom and I to visit Door County!"
United States
Kayla V.
The price is NZ$520
includes taxes & fees
10 Nov - 11 Nov
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

14. Updated Vintage 1938 Log Cabin – Walk to Sister Bay

Updated Vintage 1938 Log Cabin – Walk to Sister Bay
Sister Bay
10.0 out of 10, Exceptional, (227 reviews)
"We had a great stay in Sister Bay! Perfect location within walking distance to all shops and restaurants. Would highly recommend staying here!"
United States
Cole M.
The price is NZ$977
includes taxes & fees
17 Nov - 18 Nov
Updated Vintage 1938 Log Cabin – Walk to Sister Bay

15. Walk to Downtown! Wooded 4BR Sister Bay Home

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.8 out of 10, Exceptional, (31 reviews)
"Nice clean property close to town."
United States
Nicole H.
The price is NZ$879
includes taxes & fees
10 Nov - 11 Nov
Walk to Downtown! Wooded 4BR Sister Bay Home

16. Insta-worthy Waterfront Cottage with Hot Tub

Insta-worthy Waterfront Cottage with Hot Tub
Ellison Bay
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location with friendly and very responsive hosts!"
United States
Bart T.
The price is NZ$1,427
includes taxes & fees
10 Nov - 11 Nov
Insta-worthy Waterfront Cottage with Hot Tub

17. Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
Ellison Bay
10.0 out of 10, Exceptional, (33 reviews)
"nice quiet house to stay in thats still close to all that Door County has to offer."
United States
Jamison M.
The price is NZ$1,194
includes taxes & fees
11 Nov - 12 Nov
Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

18. Sunset Sanctuary-Bay side Bluff with Hot Tub

Sunset Sanctuary-Bay side Bluff with Hot Tub
Egg Harbor
10.0 out of 10, Exceptional, (59 reviews)
"Amazing property and all the essentials!"
United States
Jordan N.
The price is NZ$1,228
includes taxes & fees
10 Nov - 11 Nov
Sunset Sanctuary-Bay side Bluff with Hot Tub

19. Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay

Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (13 reviews)
"Smooth experience and easy communication with the host. Highly recommend!"
United States
Kristin G.
The price is NZ$1,079
includes taxes & fees
5 Dec - 6 Dec
Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay

20. Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay

Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (32 reviews)
"The house was clean and very comfortable! Everything we could have wanted was there- we discovered the drawer in the coffee table with games on night three:)Loved walking into Ellison Bay for dinner, sunsets and morning coffee.Will definitely stay here again!!"
United States
Molly C.
The price is NZ$1,150
includes taxes & fees
10 Nov - 11 Nov
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
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.
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Top Baileys Harbor Hotel Reviews

Find out more about Baileys Harbor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Baileys Harbor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Baileys Harbor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Baileys Harbor. Seeing all the best attractions is bound to make you fall in love with Baileys Harbor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Baileys Harbor short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Baileys Harbor?

Yes, there are holiday rentals close to the most popular sights in Baileys Harbor, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Baileys Harbor speak positively about the scenic lakeside and top-notch restaurants in this destination. Allow some time to check out the shops during your trip.

What are some of the best holiday rentals that Baileys Harbor has to offer?

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!: This highly rated holiday home rental in Baileys Harbor is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Baileys Harbor?

Expedia has 70 holiday rentals for your stay in Baileys Harbor.

What can I see and do in Baileys Harbor?

Lake Michigan and Kangaroo Lake are a couple of scenic spots to enjoy the outdoors, whereas Door Shakespeare is one of the cultural attractions. Door County Brewing Company and Cana Island Lighthouse are other places to visit while you're in town.

What are holiday rentals like in Baileys Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Baileys Harbor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.