An aerial view of a coastal island with a mix of residential areas, green spaces, and rocky coastlines.

Baileys Harbor Vacation Rentals

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Check prices for these dates

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

Our top choices for Baileys Harbor vacation 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.
$1,525 nightly
The price is $1,731
Oct 16 - Oct 17
Total with taxes and fees
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
$209 nightly
The price is $238
Oct 25 - Oct 26
Total with taxes and fees
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
$262 nightly
The price is $297
Oct 13 - Oct 14
Total with taxes and fees
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.
$138 nightly
The price is $157
Nov 2 - Nov 3
Total with taxes and fees
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
$275 nightly
The price is $312
Oct 4 - Oct 5
Total with taxes and fees
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
$241 nightly
The price is $273
Oct 4 - Oct 5
Total with taxes and fees
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.
$308 nightly
The price is $350
Oct 12 - Oct 13
Total with taxes and fees
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
$379 nightly
The price is $430
Oct 4 - Oct 5
Total with taxes and fees
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.
$498 nightly
The price is $537
Nov 2 - Nov 3
Total with taxes and fees
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
$142 nightly
The price is $162
Nov 2 - Nov 3
Total with taxes and fees
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.
$786 nightly
The price is $892
Oct 4 - Oct 5
Total with taxes and fees
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.
$705 nightly
The price is $800
Oct 6 - Oct 7
Total with taxes and fees
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.
$365 nightly
The price is $392
Nov 1 - Nov 2
Total with taxes and fees
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!
Two red Adirondack chairs facing a dock extending into a body of water with a clear sky above.

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.
$302 nightly
The price is $343
Oct 19 - Oct 20
Total with taxes and fees
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
$369 nightly
The price is $418
Oct 4 - Oct 5
Total with taxes and fees
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.
$1,742 nightly
The price is $1,977
Oct 9 - Oct 10
Total with taxes and fees
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.
$646 nightly
The price is $733
Oct 18 - Oct 19
Total with taxes and fees
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.
$1,010 nightly
The price is $1,146
Oct 4 - Oct 5
Total with taxes and fees
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

Gordon Lodge

Gordon Lodge

10/10 Excellent
"Very good ! Definitely recommend it to friends."
RUI E. 1-night trip
Posted 4 hours ago
Gordon Lodge

Find out more about Baileys Harbor

Everything you need to know about Baileys 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 Baileys 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 Baileys Harbor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Baileys Harbor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Baileys 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 Baileys 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 $140 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 Baileys Harbor rentals

At Expedia, we put the best Baileys 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 Baileys 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 Baileys 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 Baileys 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

Can I find vacation rentals in Baileys Harbor?

Yes, we offer vacation rentals close to top attractions in Baileys Harbor, or you can select a secluded option if you'd like a relaxing place to 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 vacation home rentals that Baileys Harbor has to offer?

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!: This highly rated vacation home rental in Baileys Harbor is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Baileys Harbor?

Expedia has 70 vacation 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 vacation rentals like in Baileys Harbor?

Vacation rentals are privately owned properties you can stay in for several days or longer in Baileys Harbor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family gatherings.