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

Baileys Harbor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Baileys Harbor vacation rentals

Aerial view

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

Dog Friendly home in Baileys Harbor near Cana Island Lighthouse
Baileys Harbor
The price is ￥110,257
￥174,203 total
includes taxes & fees
Sep 7 - Sep 8
Dog Friendly home in Baileys Harbor near Cana Island Lighthouse
Exterior

2. Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (77 reviews)
"Awesome Location! Great size for our family of 5. The pool was Nice too! "
United States
Elsy
The price is ￥39,542
￥44,881 total
includes taxes & fees
Sep 7 - Sep 8
Evergreen Hill Condominiums
Front of property - evening/night

3. Westwood Shores Waterfront Resort

Westwood Shores Waterfront Resort
3.0 star property
Sturgeon Bay
9.6 out of 10, Exceptional, (972 reviews)
"Excellent resort in a great location"
United States
Ben
The price is ￥36,805
￥41,774 total
includes taxes & fees
Sep 2 - Sep 3
Westwood Shores Waterfront Resort
Indoor pool, seasonal outdoor pool

4. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (510 reviews)
"Perfect place!"
United States
Kay
The price is ￥35,001
￥42,783 total
includes taxes & fees
Sep 2 - Sep 3
Waterbury Inn
Exterior

5. 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 ￥107,260
￥254,674 total
includes taxes & fees
Sep 15 - Sep 16
A Truly Luxurious Door County Retreat
Exterior

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, (75 reviews)
"Wonderful location, amazing accomodations, everything you could possibly need that you might have forgotten."
United States
melinda o.
The price is ￥31,858
￥36,160 total
includes taxes & fees
Sep 29 - Sep 30
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
Exterior

7. Cedar & Glass | Modern Architecture Forest Retreat

Cedar & Glass | Modern Architecture Forest Retreat
Fish Creek
9.6 out of 10, Exceptional, (4 reviews)
"Great house. Will definitely stay there again. In the woods. Easy to get to Egg Harbor or Fish Creek. Most organized VRBO ever stayed at."
United States
L B.
The price is ￥85,648
￥164,805 total
includes taxes & fees
Sep 3 - Sep 4
Cedar & Glass | Modern Architecture Forest Retreat
Property grounds

8. Bridgeport Waterfront Resort

Bridgeport Waterfront Resort
3.0 star property
Sturgeon Bay
9.0 out of 10, Wonderful, (646 reviews)
"Enjoyed my stay, no complaints"
United States
Jordan
The price is ￥34,868
￥41,574 total
includes taxes & fees
Sep 7 - Sep 8
Bridgeport Waterfront Resort
Dining

9. 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, (13 reviews)
"Excellent location! Condo was awesome with wonderful finishes. Very cozy and inviting. "
United States
Jason L.
The price is ￥68,038
￥120,295 total
includes taxes & fees
Sep 1 - Sep 2
CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.
Exterior

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, (60 reviews)
"Fantastic property - was perfect for our family of 5."
United States
Andrew L.
The price is ￥46,674
￥99,193 total
includes taxes & fees
Sep 23 - Sep 24
Private 3BR Gem on 2.5 Wooded Acres- Close to All
Smart TV, offices

11. Modern 1BD Retreat · Patio & Firepit · Egg Harbor

Modern 1BD Retreat · Patio & Firepit · Egg Harbor
Egg Harbor
10.0 out of 10, Exceptional, (94 reviews)
"Loved staying here! The Flats have such a nice layout for getaways! They had everything we needed plus a great location. Will be staying here again!"
United States
Heather M.
The price is ￥37,125
￥65,578 total
includes taxes & fees
Sep 7 - Sep 8
Modern 1BD Retreat · Patio & Firepit · Egg Harbor
TV, offices

12. Architect-Designed Flat · King · Egg Harbor

Architect-Designed Flat · King · Egg Harbor
Egg Harbor
10.0 out of 10, Exceptional, (65 reviews)
"Great location. Good communication with owners. Nice little touches (chocolate bar, beer coupon) well furnished for eating if you choose to."
United States
Shannon
The price is ￥40,588
￥70,418 total
includes taxes & fees
Sep 22 - Sep 23
Architect-Designed Flat · King · Egg Harbor
Exterior

13. Cardinal Crest of Sister Bay

Cardinal Crest of Sister Bay
Sister Bay
10.0 out of 10, Exceptional, (48 reviews)
"Fully equipped kitchen and great, secluded location."
United States
Mary R.
Cardinal Crest of Sister Bay
Interior

14. SEPTEMBER SPECIAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW

SEPTEMBER SPECIAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW
Egg Harbor
9.2 out of 10, Wonderful, (152 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 ￥27,055
￥53,849 total
includes taxes & fees
Sep 2 - Sep 3
SEPTEMBER SPECIAL! DOOR COUNTY GETAWAY @ LANDMARK RESORT - Cozy 1 BR. WOODVIEW
Interior

15. SEPTEMBER SPECIAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!

SEPTEMBER SPECIAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!
Egg Harbor
9.4 out of 10, Exceptional, (179 reviews)
"Our stay was very pleasant. Accommodations were perfect. Staff was very friendly and professional. The host was very accommodating. Will definitely stay there again."
United States
Joseph M.
The price is ￥24,350
￥47,990 total
includes taxes & fees
Sep 1 - Sep 2
SEPTEMBER SPECIAL! EGG HARBOR GETAWAY -LANDMARK RESORT Cozy 1 Bedroom Wood-view!
Property grounds

16. 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 ￥62,435
￥117,381 total
includes taxes & fees
Sep 2 - Sep 3
Sunset Sanctuary-Bay side Bluff with Hot Tub
Terrace/patio

17. Cabin on Peninsula | Waterfront + Sunset View

Cabin on Peninsula | Waterfront + Sunset View
Jacksonport
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful stay, exactly as described. Had a blast, plan on returning soon."
United States
John N.
The price is ￥140,695
￥258,835 total
includes taxes & fees
Sep 7 - Sep 8
Cabin on Peninsula | Waterfront + Sunset View
Property grounds

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

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.6 out of 10, Exceptional, (29 reviews)
"Nice clean property close to town."
United States
Nicole H.
The price is ￥50,332
￥103,767 total
includes taxes & fees
Sep 27 - Sep 28
Walk to Downtown! Wooded 4BR Sister Bay Home
Interior

19. Charming garden cottage downtown Ellison Bay walking distance to lake and shops

Charming garden cottage downtown Ellison Bay walking distance to lake and shops
Ellison Bay
9.8 out of 10, Exceptional, (133 reviews)
"Just couldn’t be better, great location, exemplary cleanliness, so comfortable. The host was extremely responsive and we would absolutely stay there again"
United States
James
The price is ￥36,020
￥62,324 total
includes taxes & fees
Sep 9 - Sep 10
Charming garden cottage downtown Ellison Bay walking distance to lake and shops
Interior

20. Family Retreat | Game Room + EV Charger

Family Retreat | Game Room + EV Charger
Sturgeon Bay
10.0 out of 10, Exceptional, (2 reviews)
"Excellent stay! Loved the house layout and the private lot!"
United States
Paul L.
The price is ￥55,231
￥148,298 total
includes taxes & fees
Sep 20 - Sep 21
Family Retreat | Game Room + EV Charger
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Baileys Harbor Hotel Reviews

Settlement Inn & Lavender Spa

Settlement Inn & Lavender Spa

10/10 Excellent
"Really like the small kitchen area right in our room. Nice little continental breakfast. Nice location. Very friendly and courteous staff!"
Christine 3-night trip
Posted 10 hours ago
Settlement Inn & Lavender Spa

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
  • Use the map to find apartments and other holiday homes in the Baileys Harbor neighbourhood you prefer
  • 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 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?

Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!: This highly rated vacation home rental in Baileys Harbor is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation 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.