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Baileys Harbor Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Baileys Harbor holiday rentals

A loft-style living space with a high ceiling, a wooden staircase, a patterned sofa, a grey couch, and a small table with a lamp.

1. Dog Friendly home in Baileys Harbor near Cana Island Lighthouse

Dog Friendly home in Baileys Harbor near Cana Island Lighthouse
Baileys Harbor
Dog Friendly home in Baileys Harbor near Cana Island Lighthouse
A deck with a blue umbrella, wicker baskets, and a welcome mat.

2. Beautiful Home in Baileys Harbor

Beautiful Home in Baileys Harbor
Baileys Harbor
10.0 out of 10, Exceptional, (47 reviews)
"We had a wonderful time and home was perfect! Owners were very friendly and nice."
United States
Denise Z.
The price is HK$5,720
HK$13,585 total
includes taxes & fees
16 Oct - 17 Oct
Beautiful Home in Baileys Harbor
An indoor swimming pool with a 3ft depth marker, surrounded by lounge chairs and a wooden ceiling.

3. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (520 reviews)
"It was a nice private quiet place!"
United States
Elizabeth
The price is HK$1,514
HK$1,867 total
includes taxes & fees
25 Oct - 26 Oct
Waterbury Inn
A multi-story building with a central staircase, surrounded by trees and a well-maintained lawn.

4. Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (79 reviews)
"Awesome Location! Great size for our family of 5. The pool was Nice too! "
United States
Elsy
The price is HK$2,056
HK$2,333 total
includes taxes & fees
13 Oct - 14 Oct
Evergreen Hill Condominiums
A white two-story house with a wooden deck and a small porch.

5. 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, (80 reviews)
"We had an amazing stay! The house was very accommodating and was a great location!!!"
United States
Natalie L.
The price is HK$1,083
HK$1,229 total
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
A room with large windows offering a view of a forest and the ocean.

6. AUTUMN DEAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!

AUTUMN DEAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!
Egg Harbor
9.4 out of 10, Exceptional, (185 reviews)
"the property was kinda small. not too clean, there were cab webs in the bathroom."
United States
Mary Elizabeth
The price is HK$1,264
HK$2,450 total
includes taxes & fees
4 Oct - 5 Oct
AUTUMN DEAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!
A poolside area with chairs and tables, a lamp post, and a view of the sunset over the water.

7. Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (980 reviews)
"We had a wonderful stay at this resort! The property was beautiful, well-maintained, and provided the perfect setting for a relaxing vacation. The staff was friendly, welcoming, and attentive, and everything was clean and comfortable. We especially enjoyed the beautiful surroundings and peaceful atmosphere. It was a wonderful experience, and we would happily return!"
United States
Lisa
The price is HK$1,890
HK$2,145 total
includes taxes & fees
4 Oct - 5 Oct
Westwood Shores Waterfront Resort
A room with large windows offering a view of a forest and the ocean.

8. AUTUMN DEAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW

AUTUMN DEAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW
Egg Harbor
9.2 out of 10, Wonderful, (156 reviews)
"We love The Landmark Resort. It’s our favorite place to stay when visiting Door County. The condo was clean and comfortable."
United States
Nicole D.
The price is HK$1,405
HK$2,747 total
includes taxes & fees
12 Oct - 13 Oct
AUTUMN DEAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW
A cozy living room with a wooden ceiling, a beige sofa, a white armchair, and a small table.

9. Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
Sister Bay
9.8 out of 10, Exceptional, (57 reviews)
"One of the best places to stay near Sister Bay. The location is very convenient but quieter, the house is cute and well equipped with all the items we need, and the spacious backyard is a huge bonus!"
United States
Katherine
The price is HK$1,107
HK$3,376 total
includes taxes & fees
4 Oct - 5 Oct
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
A two-story house with a wrap-around porch, a turret, and a front door with an American flag.

10. 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 HK$1,774
HK$4,216 total
includes taxes & fees
2 Nov - 3 Nov
Private 3BR Gem on 2.5 Wooded Acres- Close to All
A waterfront property with a paved walkway, a stone retaining wall, and a large building with multiple balconies.

11. Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (665 reviews)
"Great location and beautiful views."
United States
John
The price is HK$1,036
HK$1,270 total
includes taxes & fees
2 Nov - 3 Nov
Bridgeport Waterfront Resort
A modern living room with a stone fireplace, large windows, and a cozy seating area.

12. Cedar & Glass | Modern Architectural Retreat

Cedar & Glass | Modern Architectural Retreat
Fish Creek
9.6 out of 10, Exceptional, (5 reviews)
"A thoughtfully designed and curated home with top end amenities. We stayed for 3 nights and loved the serenity of the setting and space. The house has gorgeous showers, a gas fireplace and fun games to play. Loved being able to make all kinds of coffee drinks on the espresso machine. Perfect place to stay and enjoy nature and decompress. Highly recommended!!!"
United States
katherine k.
The price is HK$3,359
HK$7,001 total
includes taxes & fees
4 Oct - 5 Oct
Cedar & Glass | Modern Architectural Retreat
A lakeside seating area with Adirondack chairs and a fire pit, surrounded by trees and string lights.

13. Stunning Waterfront Cottage | Private Dock + Hot Tub

Stunning Waterfront Cottage | Private Dock + Hot Tub
Ellison Bay
10.0 out of 10, Exceptional, (42 reviews)
"Great house in a great location with friendly and very responsive hosts!"
United States
Bart T.
The price is HK$1,929
HK$6,279 total
includes taxes & fees
6 Oct - 7 Oct
Stunning Waterfront Cottage | Private Dock + Hot Tub
A modern living room with a fireplace, a ceiling fan, and a large window with a view of trees.

14. CONDO 5-Sister Bay Gem-Steps to the Beach

CONDO 5-Sister Bay Gem-Steps to the Beach
Sister Bay
10.0 out of 10, Exceptional, (21 reviews)
"Great place and location! "
United States
Kim B.
The price is HK$1,167
HK$3,076 total
includes taxes & fees
1 Nov - 2 Nov
CONDO 5-Sister Bay Gem-Steps to the Beach
A swimming pool with a white fence, a small shed, and a grassy yard.

15. Cozy Cabin! Amazing Location in Fish Creek! Pool!

Cozy Cabin! Amazing Location in Fish Creek! Pool!
Fish Creek
9.4 out of 10, Exceptional, (118 reviews)
"Nice place to stay in Door County. Very centralized and walkable to town."
United States
Paul E.
Cozy Cabin! Amazing Location in Fish Creek! Pool!
A grassy yard with a house, trees, and a bench.

16. Waterfront 1 bedroom and loft cottage with small private pier on Garrett Bay

Waterfront 1 bedroom and loft cottage with small private pier on Garrett Bay
Ellison Bay
9.6 out of 10, Exceptional, (144 reviews)
"We had a great stay. Location was private and had beautiful views on the water!"
United States
Katherine S.
The price is HK$1,483
HK$2,690 total
includes taxes & fees
19 Oct - 20 Oct
Waterfront 1 bedroom and loft cottage with small private pier on Garrett Bay
A cozy living room with a wooden ceiling, a beige sofa, a white armchair, and a small table.

17. Updated Home w/ Deck: 2 Mi to Sister Bay Beach!

Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
3.0 star property
Sister Bay
The price is HK$1,452
HK$3,282 total
includes taxes & fees
4 Oct - 5 Oct
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
A two-story house with a front porch, a garage, and a landscaped garden with various plants and flowers.

18. A Truly Luxurious Door County Retreat

A Truly Luxurious Door County Retreat
Fish Creek
9.6 out of 10, Exceptional, (23 reviews)
"Communication was easy and straight forward, accomidations fit our group perfectly. Great location for the outdoor activities we planned."
United States
Brant F.
The price is HK$6,681
HK$15,517 total
includes taxes & fees
9 Oct - 10 Oct
A Truly Luxurious Door County Retreat
Property grounds

19. Sunset Sanctuary-Bay side Bluff with Hot Tub

Sunset Sanctuary-Bay side Bluff with Hot Tub
Egg Harbor
10.0 out of 10, Exceptional, (57 reviews)
"Amazing property and all the essentials!"
United States
Jordan N.
The price is HK$3,061
HK$5,754 total
includes taxes & fees
18 Oct - 19 Oct
Sunset Sanctuary-Bay side Bluff with Hot Tub
A cabin with a deck, surrounded by forest, and a body of water in front.

20. A Classic Waterfront A-Frame on Rowley’s Bay

A Classic Waterfront A-Frame on Rowley’s Bay
Sister Bay
10.0 out of 10, Exceptional, (27 reviews)
"Beautiful property and perfect location! Thank you!"
United States
Nicole N.
The price is HK$4,142
HK$8,992 total
includes taxes & fees
4 Oct - 5 Oct
A Classic Waterfront A-Frame on Rowley’s 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

The Landing Resort

The Landing Resort

10/10 Excellent
"Loved it"
Robert 3-night trip
Posted less than an hour ago
The Landing Resort

Find out more about Baileys Harbor

Search for holiday rentals in Baileys Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Baileys Harbor using one of the methods below:

  • View our selection of featured holiday rentals in Baileys Harbor
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  • Enter your travel dates to view the best deals on holiday rentals in Baileys Harbor while they last

Look no further and take a look at our great range of rental properties in Baileys Harbor!

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.