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Baileys Harbor Holiday Rentals

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Holiday Rentals in Baileys Harbor

Serene Lakefront Baileys Harbor Home w/ Deck!

9.6 out of 10, Exceptional, (71)
" Beautiful view, quiet, peaceful! Would love to visit again! Affordable. "
Serene Lakefront Baileys Harbor Home w/ Deck!

Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

10.0 out of 10, Exceptional, (227)
"My husband and I have done a number of VRBO rentals over the years. This one ranks in the Top 5. It is a comfortable home and one of the better stocked homes. The view of Lake Michigan, even from inside the home, is gorgeous. Everything about our stay was easy. We highly recommend this home."
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Stunning Studio just steps from the Bjorklunden Trail System in Baileys Harbor

9.8 out of 10, Exceptional, (30)
"Quiet neighborhood hust outside of down town Baileys Harbor. It was everything my girlfriend and I needed for the weekend. It's a perfect spot for a couples trip."
Stunning Studio just steps from the Bjorklunden Trail System in Baileys Harbor

Scandinavian Lodge

3.5 star property
9.4 out of 10, Exceptional, (1356)
"We have stayed here a few times. Nice place. Great pool. "
The price is AU$226
includes taxes & fees
25 Nov - 26 Nov
Scandinavian Lodge

Bridgeport Waterfront Resort

3.0 star property
9.0 out of 10, Wonderful, (419)
"Hotel location is great and walkable. Room was clean and bed was comfortable. Room has a full kitchen for the convenience of families staying there. "
The price is AU$227
includes taxes & fees
25 Nov - 26 Nov
Bridgeport Waterfront Resort

Westwood Shores Waterfront Resort

3.0 star property
9.6 out of 10, Exceptional, (799)
"Excellent experience, was very happy we upgraded to a 2 bedroom suite. Everything was impeccable, linens high quality, kitchen had everything one could need. Friendly staff."
The price is AU$155
includes taxes & fees
1 Dec - 2 Dec
Westwood Shores Waterfront Resort

Waterbury Inn

2.5 star property
9.0 out of 10, Wonderful, (441)
"Very helpful "
The price is AU$246
includes taxes & fees
25 Nov - 26 Nov
Waterbury Inn

Landmark Resort

3.5 star property
9.2 out of 10, Wonderful, (466)
"Great location!"
Landmark Resort

Amore' De Bay Romantic Suite for 2 includes Free Continental Breakfast & WiFi.

9.8 out of 10, Exceptional, (200)
"What an awesome experience! 1st time in the area. Went sightseeing,found beautiful waterfalls within an hours drive! Not an extremely hectic area. Easy to get around.lots to see and shops to visit. Our hosts Bob and Bonnie were delightful! Will definitely stay again!hosts Bob and "
Amore' De Bay Romantic Suite for 2 includes Free Continental Breakfast & WiFi.

Clean Cozy Door County Cottage. Waterfront Property, WiFi.

9.8 out of 10, Exceptional, (112)
"What a great stay. Everything we hoped for. Great host!!!"
Clean Cozy Door County Cottage. Waterfront Property, WiFi.

Downtown Sturg - Arcades/Theater/Modern

9.6 out of 10, Exceptional, (18)
"This was w wonderful house to stay in! Would absolutely stay here again! "
Downtown Sturg - Arcades/Theater/Modern

Waterfront Swedish-style Log Cabin on Sand Bay, Door County - Moonlight Magic

9.8 out of 10, Exceptional, (317)
"This was our second year staying here and will definitely come back again. The home is very comfortable, the view spectacular and it is so peaceful! A great place to escape from the business of life and take a breath. "
Waterfront Swedish-style Log Cabin on Sand Bay, Door County - Moonlight Magic

Spectacular water view condo!

9.6 out of 10, Exceptional, (229)
"My wife and I rented this property for a long weekend to see the fall leaves. It has a nice view of Green Bay and is centrally located to parks and little towns. Landmark and this specific condo are great for a cozy weekend. The condo was clean and comfortable."
The price is AU$300
includes taxes & fees
1 Dec - 2 Dec
Spectacular water view condo!

Waterfront Dream Cottage With A Million Dollar View, HARBOR Unit

10.0 out of 10, Exceptional, (146)
"Perfect location right on the water. The house is very comfortable. Bathroom with sauna and heated floors is definitely a perk"
Waterfront Dream Cottage With A Million Dollar View, HARBOR Unit

Country Estate! Pool, Game Room, Sauna

10.0 out of 10, Exceptional, (45)
"The cleaning cost was very high! It needed detailed cleaning, bed broke, loved the house(s) pool sauna firepit! We enjoyed our stay"
The price is AU$2,415
includes taxes & fees
5 Dec - 6 Dec
Country Estate! Pool, Game Room, Sauna

Treehouse at Plum Bottom *Voted Best of Door County

9.8 out of 10, Exceptional, (79)
"Wonderful and peaceful location away from the crowds."
Treehouse at Plum Bottom *Voted Best of Door County

Sherwood Lighthouse Cabin - Near Boat Launch & State Park

9.6 out of 10, Exceptional, (36)
"The cottage is in a rural setting but close to many attractions. Enjoy long walks with a canopy of trees and wildlife. Beautiful sunsets available with water views. A lighthouse is just across the road. Sturgeon Bay has many unique shops and restaurants to enjoy. Day trips to Door County are doable."
Sherwood Lighthouse Cabin - Near Boat Launch & State Park

Modern condo in scenic Egg Harbor! Heart of Door County!

9.4 out of 10, Exceptional, (179)
"Wasn't to far from the places we wanted to go and see. I wasnt sire what to expect it being a condo, but was not expecting it to be where it was. Didnt like that we had to walk to fitness center/pool. I assumed these were in the same building that we were in. Didnt hear really any noise so that was nice. Didnt hear much of any noise i "
Modern condo in scenic Egg Harbor! Heart of Door County!

Clean Cozy Cottage On Waterfront Property Privacy Yet Close To Town

10.0 out of 10, Exceptional, (87)
"Quant, quiet cabins with a bit of nostalgia. Perfect size for our friends getaway weekend , a couples retreat or small family getaway. Very clean and I loved the nostalgia of the inside. Beautiful water view to watch the sunset at night. Just far enough out of town for quietness, but close enough for convenience and other things to do. Host was very nice and informative. Would definitely stay here again!"
Clean Cozy Cottage On Waterfront Property Privacy Yet Close To Town

Stunning Door County Cabin In The Woods, Wi-Fi, Firepit, Fireplace, Game Room

10.0 out of 10, Exceptional, (511)
"Stayed here several times and never disappoints. Clean, all the amenities you could want, quiet but close to everything. Love it!"
Stunning Door County Cabin In The Woods, Wi-Fi, Firepit, Fireplace, Game Room
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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Other types of properties in Baileys Harbor you may be interested in

Gordon Lodge

4.0 star property
9.4 out of 10, Exceptional, (1006)
"Best place to stay in Door County. Nice pool, hot tub, great grounds and breakfast! "
Gordon Lodge

Beachfront Inn

2.0 star property
9.4 out of 10, Exceptional, (262)
"We arrived later in the afternoon but were greeted by the owners who were so friendly! It was nice feeling like we were expected."
Beachfront Inn

Ridges Inn & Suites

2.5 star property
7.8 out of 10, Good, (436)
"Enjoyed the nearby Ridges walking trails and lighthouse. Convenient travel to several state and county parks. Roomy accommodations and fireplace was nice to have available during the cooler fall time of year that we visited."
Ridges Inn & Suites
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Sister Bay Vintage Log Cabin - Recent Remodel: This holiday home rental outside of Baileys Harbor offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books. Another good choice for your trip to Baileys Harbor is Serene Lakefront Baileys Harbor Home w/ Deck!.

How many holiday rentals will I find in Baileys Harbor?

Expedia has 66 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 Stone's Throw Winery 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.