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

Baileys Harbor Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Baileys Harbor holiday rentals

Living area

1. Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views

Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views
Baileys Harbor
9.4 out of 10, Exceptional, (15 reviews)
"This booking was better than expected. The location is super close to everything, good pricing and the views right on the lake are awesome too. It provides everything needed to have a good weekend away! Kayak, grills, a cozy place to sleep in. I’m always afraid to book places because I’m very picky when it comes to places and being clean. I did not notice any issues with that, so that was a huge plus for me. Will consider back booking here when I come back in the future!"
United States
Sarai
The price is HK$1,785
HK$3,824 total
includes taxes & fees
9 Sept - 10 Sept
Lakefront Cottage Retreat w/ Private Dock, Paddle Boards, Fire Pit, Sunset Views
Room

2. 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 HK$5,227
HK$8,317 total
includes taxes & fees
21 Sept - 22 Sept
Dog Friendly home in Baileys Harbor near Cana Island Lighthouse
Terrace/patio

3. Waterfront Escape at the Tip of Door County

Waterfront Escape at the Tip of Door County
Ellison Bay
10.0 out of 10, Exceptional, (79 reviews)
"Amazing location and property. Enjoyed the neighboring vicinity for great runs and scenic vistas."
United States
Tracy S.
The price is HK$5,248
HK$11,042 total
includes taxes & fees
30 Sept - 1 Oct
Waterfront Escape at the Tip of Door County
Pool

4. 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, (142 reviews)
"We had a great stay. Location was private and had beautiful views on the water!"
United States
Katherine S.
The price is HK$1,717
HK$2,990 total
includes taxes & fees
19 Sept - 20 Sept
Waterfront 1 bedroom and loft cottage with small private pier on Garrett Bay
Interior

5. 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 HK$1,764
HK$3,052 total
includes taxes & fees
10 Sept - 11 Sept
Charming garden cottage downtown Ellison Bay walking distance to lake and shops
Property grounds

6. Relax on the Bay — Kayaks, Hot Tub & Firepit Nights

Relax on the Bay — Kayaks, Hot Tub & Firepit Nights
Ellison Bay
10.0 out of 10, Exceptional, (38 reviews)
"Great house in a great location with friendly and very responsive hosts!"
United States
Bart T.
The price is HK$2,054
HK$6,440 total
includes taxes & fees
10 Sept - 11 Sept
Relax on the Bay — Kayaks, Hot Tub & Firepit Nights
Property grounds

7. 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 HK$2,173
HK$4,721 total
includes taxes & fees
20 Sept - 21 Sept
Walk to Downtown! Wooded 4BR Sister Bay Home
Living area

8. CONDO 7-Coastal Chic Condo in the Heart of Sister Bay!

CONDO 7-Coastal Chic Condo in the Heart of Sister Bay!
Sister Bay
10.0 out of 10, Exceptional, (35 reviews)
"All around a wonderful location."
United States
Kim K.
The price is HK$2,765
HK$5,156 total
includes taxes & fees
20 Sept - 21 Sept
CONDO 7-Coastal Chic Condo in the Heart of Sister Bay!
Interior

9. 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$1,450
HK$3,279 total
includes taxes & fees
15 Sept - 16 Sept
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
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 HK$2,351
HK$4,938 total
includes taxes & fees
23 Sept - 24 Sept
Private 3BR Gem on 2.5 Wooded Acres- Close to All
Exterior

11. 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$6,002
HK$14,632 total
includes taxes & fees
17 Sept - 18 Sept
A Truly Luxurious Door County Retreat
Indoor pool

12. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (512 reviews)
"It was a nice private quiet place!"
United States
Elizabeth
The price is HK$1,936
HK$2,348 total
includes taxes & fees
14 Sept - 15 Sept
Waterbury Inn
Living area

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

CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
Sister Bay
10.0 out of 10, Exceptional, (22 reviews)
"This condo is awesome, brand new, beautiful and can’t beat the location! Our host was very communicative and helpful! Very well apportioned kitchen and bathrooms. Would highly recommend and plan to stay here again! "
United States
Sean O.
The price is HK$2,765
HK$5,156 total
includes taxes & fees
13 Sept - 14 Sept
CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
Living area

14. 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, (56 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$1,105
HK$3,372 total
includes taxes & fees
15 Sept - 16 Sept
Updated Home w/ Deck: 2 Mi to Sister Bay Beach!
Terrace/patio

15. 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 HK$7,350
HK$13,287 total
includes taxes & fees
1 Oct - 2 Oct
Cabin on Peninsula | Waterfront + Sunset View
Interior

16. Cedar & Glass | Modern Architecture Forest Retreat

Cedar & Glass | Modern Architecture Forest Retreat
Fish Creek
9.6 out of 10, Exceptional, (4 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$4,194
HK$8,079 total
includes taxes & fees
21 Sept - 22 Sept
Cedar & Glass | Modern Architecture Forest Retreat
Exterior

17. 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 HK$1,936
HK$2,198 total
includes taxes & fees
9 Sept - 10 Sept
Evergreen Hill Condominiums
Exterior

18. 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)
"We had an amazing stay! The house was very accommodating and was a great location!!!"
United States
Natalie L.
The price is HK$1,427
HK$1,619 total
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
Living area

19. 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 HK$1,724
HK$3,104 total
includes taxes & fees
10 Sept - 11 Sept
Architect-Designed Flat · King · Egg Harbor
Living area

20. Designer Studio Flat · Heated Floors · Egg Harbor

Designer Studio Flat · Heated Floors · Egg Harbor
Egg Harbor
9.8 out of 10, Exceptional, (94 reviews)
"First time staying here and we will be back!"
United States
Anne R.
The price is HK$1,737
HK$3,120 total
includes taxes & fees
20 Sept - 21 Sept
Designer Studio Flat · Heated Floors · Egg Harbor
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

Scandinavian Lodge

Scandinavian Lodge

10/10 Excellent
"The 2 bedroom unit was perfect for our family. It was an easy walk from here to downtown Sister Bay. There's a grocery store very close so you can stock up the full size refrigerator with whatever you want. My only complaint would be the mattress was extremely uncomfortable and my back was pretty sore every morning after trying to sleep on it."
Jason 2-night trip
Posted 2 hours ago
Scandinavian Lodge

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?

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