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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Baileys Harbor vacation rentals

A spacious kitchen with a large island, a dining area with a sofa, and a fireplace.

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, (115 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.
$457 nightly
The price is $519
Nov 9 - Nov 10
Total with taxes and fees
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
A large hotel with multiple balconies, a swimming pool, and a well-maintained lawn.

2. Scandinavian Lodge

Scandinavian Lodge
3.5 star property
Sister Bay
9.4 out of 10, Exceptional, (1,728 reviews)
"Wonderful staff and very clean resort!"
United States
Shannon
$125 nightly
The price is $143
Nov 15 - Nov 16
Total with taxes and fees
Scandinavian Lodge
A multi-story building with a central staircase, surrounded by trees and a well-maintained lawn.

3. Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (82 reviews)
"Awesome Location! Great size for our family of 5. The pool was Nice too! "
United States
Elsy
$137 nightly
The price is $156
Nov 8 - Nov 9
Total with taxes and fees
Evergreen Hill Condominiums
A poolside area with chairs and tables, a lamp post, and a view of the sunset over the water.

4. Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (987 reviews)
"The homey feel and central location."
United States
Cindy
$109 nightly
The price is $124
Nov 15 - Nov 16
Total with taxes and fees
Westwood Shores Waterfront Resort
A resort with a swimming pool, outdoor seating, and multiple buildings surrounded by trees.

5. Landmark Resort

Landmark Resort
3.5 star property
Egg Harbor
9.0 out of 10, Wonderful, (706 reviews)
"Beautiful property with spacious rooms and the staff helped me during my stay."
United States
Romaine
$192 nightly
The price is $218
Nov 8 - Nov 9
Total with taxes and fees
Landmark Resort
A white two-story house with a wooden deck and a small porch.

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.
$138 nightly
The price is $157
Nov 8 - Nov 9
Total with taxes and fees
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
An indoor swimming pool with a 3ft depth marker, surrounded by lounge chairs and a wooden ceiling.

7. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (529 reviews)
"Great place to stay-beautiful location with great amenities"
United States
Megan
$207 nightly
The price is $236
Nov 8 - Nov 9
Total with taxes and fees
Waterbury Inn
A waterfront property with a paved walkway, a stone retaining wall, and a large building with multiple balconies.

8. Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (703 reviews)
"Very nice stay."
United States
Brenda
$142 nightly
The price is $162
Nov 9 - Nov 10
Total with taxes and fees
Bridgeport Waterfront Resort
A white arched entrance with a dark green door, surrounded by greenery and a pathway leading to a porch.

9. 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.
$256 nightly
The price is $292
Nov 8 - Nov 9
Total with taxes and fees
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
A modern living room with a fireplace, a ceiling fan, and a large window with a view of trees.

10. 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, (22 reviews)
"Great place and location! "
United States
Kim B.
$347 nightly
The price is $371
Nov 8 - Nov 9
Total with taxes and fees
CONDO 5-Sister Bay Gem-Steps to the Beach
A two-story house with a wrap-around porch, a turret, and a front door with an American flag.

11. 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.
$474 nightly
The price is $510
Nov 9 - Nov 10
Total with taxes and fees
Private 3BR Gem on 2.5 Wooded Acres- Close to All
A wooden deck with a table and bench, large windows with a forest view, and a sliding glass door leading to an interior with a sofa and ceiling fan.

12. Spacious Jacksonport Woodland Cabin: Screened Porch, Near Cave Point & Lake Park

Spacious Jacksonport Woodland Cabin: Screened Porch, Near Cave Point & Lake Park
Sturgeon Bay
10.0 out of 10, Exceptional, (8 reviews)
"Great place!"
United States
Anne W.
$380 nightly
The price is $431
Nov 9 - Nov 10
Total with taxes and fees
Spacious Jacksonport Woodland Cabin: Screened Porch, Near Cave Point & Lake Park
A dining area with a round glass table and two chairs, a potted plant, and a view of a street through a window with blinds.

13. Cozy Door County home with detached yoga room- short walk from Potawatomi Park

Cozy Door County home with detached yoga room- short walk from Potawatomi Park
Sturgeon Bay
10.0 out of 10, Exceptional, (58 reviews)
"Location is good. Easy bike ride to potawami State Park and downtown sturgeon Bay. It is on highway C which does get a bit of traffic but we didn't notice with the windows closed. The shower is small but functional. The two-car garage is great for storing our e-bikes. We had a very good stay. Price was very good and much nicer staying here than in the hotel."
United States
MARK w
$202 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
Cozy Door County home with detached yoga room- short walk from Potawatomi Park
A rustic cabin with a stone exterior and a red balcony, surrounded by trees.

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, (226 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.
$482 nightly
The price is $550
Nov 17 - Nov 18
Total with taxes and fees
Updated Vintage 1938 Log Cabin – Walk to Sister Bay
A living room with a sofa, a coffee table, and a window with a view of trees.

15. [Cozy] loft - steps to downtown!

[Cozy] loft - steps to downtown!
Sturgeon Bay
9.6 out of 10, Exceptional, (45 reviews)
"Excellent stay! Will definitely be recommending to others!"
United States
Autumn M.
$260 nightly
The price is $282
Nov 17 - Nov 18
Total with taxes and fees
[Cozy] loft - steps to downtown!
A backyard with two blue Adirondack chairs, a fire pit, and a house in the background.

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

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.6 out of 10, Exceptional, (30 reviews)
"Nice clean property close to town."
United States
Nicole H.
$476 nightly
The price is $512
Nov 8 - Nov 9
Total with taxes and fees
Walk to Downtown! Wooded 4BR Sister Bay Home
A modern living room with a fireplace, a dining area, and a kitchen with a bar.

17. 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.
$347 nightly
The price is $371
Nov 8 - Nov 9
Total with taxes and fees
CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
A marina with boats docked, a wooden walkway leading to the water, and a grassy area with a tree providing shade.

18. Snug Harbor Inn - Cottage 1A

Snug Harbor Inn - Cottage 1A
Sturgeon Bay
9.6 out of 10, Exceptional, (20 reviews)
"Snug Harbor is a cute place to stay right on the water. Wish we could have been there longer. The room was clean and cozy. There were fire pits out front next to the water."
United States
Maria M.
$141 nightly
The price is $161
Nov 10 - Nov 11
Total with taxes and fees
Snug Harbor Inn - Cottage 1A
Terrace/patio

19. 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.
$575 nightly
The price is $652
Nov 8 - Nov 9
Total with taxes and fees
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
A modern room with a large window, a dining table, and a bench.

20. CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.

CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.
Sister Bay
10.0 out of 10, Exceptional, (20 reviews)
"Excellent location! Condo was awesome with wonderful finishes. Very cozy and inviting. "
United States
Jason L.
$347 nightly
The price is $371
Nov 30 - Dec 1
Total with taxes and fees
CONDO 4-Luxury Loft Retreat in Downtown 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

The Landing Resort

The Landing Resort

10/10 Excellent
"We stayed in the Spinnaker Loft and it was perfect for my family of four. The small bedroom and loft gave everyone room to spread out, and the kitchen let us save money by cooking several meals instead of going out all the time. The pool and hot tub were great (with lots of towels!) and my younger son enjoyed the playground. There is free coffee in the lobby and a nice selection of board games that can be borrowed. Everything was clean and well-maintained and the staff were friendly and helpful. I would definitely stay here again the next time I'm in Door county. Oh, and don't miss the Swedish coffee place across the street - amazing cinnamon rolls!"
Melissa 3-night trip
Posted 3 hours ago
The Landing Resort

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 $124 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.