
Baileys Harbor Holiday Rentals
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Our top choices for Baileys Harbor holiday rentals

1. Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
2. Landmark Resort
Landmark Resort
3. Scandinavian Lodge
Scandinavian Lodge
4. Evergreen Hill Condominiums
Evergreen Hill Condominiums
5. Waterbury Inn
Waterbury Inn
6. Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
7. Westwood Shores Waterfront Resort
Westwood Shores Waterfront Resort
8. Private 3BR Gem on 2.5 Wooded Acres- Close to All
Private 3BR Gem on 2.5 Wooded Acres- Close to All
9. CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
10. Bridgeport Waterfront Resort
Bridgeport Waterfront Resort
11. Jacksonport Woodland Hearth Retreat - Near Lake Michigan
Jacksonport Woodland Hearth Retreat - Near Lake Michigan
12. Harbor View Penthouse Downtown Egg Harbor
Harbor View Penthouse Downtown Egg Harbor
13. THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
14. Updated Vintage 1938 Log Cabin – Walk to Sister Bay
Updated Vintage 1938 Log Cabin – Walk to Sister Bay
15. Walk to Downtown! Wooded 4BR Sister Bay Home
Walk to Downtown! Wooded 4BR Sister Bay Home
16. Insta-worthy Waterfront Cottage with Hot Tub
Insta-worthy Waterfront Cottage with Hot Tub
17. Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
18. Sunset Sanctuary-Bay side Bluff with Hot Tub
Sunset Sanctuary-Bay side Bluff with Hot Tub
19. Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
20. Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister BayFind holiday rentals that suit your style
Top Baileys Harbor Hotel Reviews

Bridgeport Waterfront Resort
Find out more about Baileys Harbor
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Baileys Harbor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Baileys Harbor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Baileys Harbor. Seeing all the best attractions is bound to make you fall in love with Baileys Harbor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Baileys Harbor short-term rentals, that won’t be hard to do.
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