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Holiday Rentals in Baileys Harbor

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Holiday Rentals in Baileys Harbor

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

8.6 out of 10, Excellent, (111)
"Great property within walking distance of anything you would want in Bailey’s Harbor"
Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

Red Cherry Woods Cottage 🍒 New Construction!

10.0 out of 10, Exceptional, (47)
"Lovely A-frame on wooded lot. Well appointed inside- comfortable and nice bedding. Beautiful view of the woods from the master bedroom. Excellent water pressure in shower. Nice white towels. We had most everything we needed in the kitchen. No complaints. Would definitely stay again! We were on a winter getaway. Will go back when we can enjoy the patio :O) "
Red Cherry Woods Cottage 🍒 New Construction!

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

10.0 out of 10, Exceptional, (232)
"The house is lovely, with all the amenities you need for a quiet time away. Being right on the lake was really nice "
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!

Cute Cottage - Center of the Door Peninsula - Pet Friendly! On Snowmobile Trail!

9.8 out of 10, Exceptional, (45)
"The cottage was center in the county so it made it very easy to get to the different places we went to. The county has so much to see and do. The three state parks are always great place for hiking. Thank you "
Cute Cottage - Center of the Door Peninsula - Pet Friendly! On Snowmobile Trail!

Scandinavian Lodge

3.5 star property
9.4 out of 10, Exceptional, (1372)
"Scandanavian lodge is awesome and the rates are great off season … Call the hotel directly first. "
The price is €140
includes taxes & fees
18 Feb - 19 Feb
Scandinavian Lodge

Landmark Resort

3.5 star property
9.2 out of 10, Wonderful, (466)
"Great location!"
The price is €145
includes taxes & fees
18 Feb - 19 Feb
Landmark Resort

Bridgeport Waterfront Resort

3.0 star property
9.0 out of 10, Wonderful, (440)
"We had a wonderful time. Our room was very clean and comfortable. Beautiful view of the water. Staff was friendly. We have stayed at a few other places in Sturgeon Bay but Bridgeport is our favorite. We book our stay for January and have stayed here 6 times in the last 10 years. My husband and I are in our 60's and are accustomed to using the stairs and seldom use an elevator. There is one elevator and the halls are long. Our favorite room is at the far end of the hall so there is a fair amount...
The price is €141
includes taxes & fees
18 Feb - 19 Feb
Bridgeport Waterfront Resort

Westwood Shores Waterfront Resort

3.0 star property
9.6 out of 10, Exceptional, (826)
"I love Westwood Shores but they recently installed new ceiling fans which are controlled solely by remote. The problem is that other unit's remote controls affected the fans/lights in our unit. Lights were coming off and on as was fan due to another guest trying to adjust their ceiling fan/light. Love the look of the fans but something needs to be done about the remote function. Otherwise, nothing but wonderful things to say about Westwood Shores. "
The price is €107
includes taxes & fees
18 Feb - 19 Feb
Westwood Shores Waterfront Resort

Waterbury Inn

2.5 star property
9.0 out of 10, Wonderful, (451)
"The check in was easy and receptionist was friendly. Overall very clean and appealing. The bed was a bit too firm for us, but the room was comfortable and clean. The receptionist during the day was less than friendly. Would most likely stay again. "
The price is €153
includes taxes & fees
18 Feb - 19 Feb
Waterbury Inn

Indoor Pool, Game RM, Movie RM! Sleep 24! Private!

10.0 out of 10, Exceptional, (49)
"Set up for family entertainment indoors"
The price is €1,608
includes taxes & fees
20 Mar - 21 Mar
Indoor Pool, Game RM, Movie RM! Sleep 24! Private!

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

9.8 out of 10, Exceptional, (320)
"Our friend group stayed here for the fifth year in a row. We love this property, and the owner always make us feel very welcome!"
Waterfront Swedish-style Log Cabin on Sand Bay, Door County - Moonlight Magic

One-of-a-Kind Rustic Retreat in Dtwn Sturgeon Bay!

9.6 out of 10, Exceptional, (52)
"Very quiet and relaxing nice little place. Would stay here again."
One-of-a-Kind Rustic Retreat in Dtwn Sturgeon Bay!

Spectacular water view condo!

9.6 out of 10, Exceptional, (239)
"My wife and I stayed here at the end of January 2025, was a great little place, mostly quiet (at that time of year), nice amenities nearby (indoor pool, hot tub, fireplace in the common area, etc), ice machine was fairly difficult to find (establishment should put up some directions/instructions), but overall it was a peaceful, relaxing weekend for the two of us. The only downsides were 1) noises from people walking loudly on the floor above us 2) folks letting the doors slam shut as they...
The price is €176
includes taxes & fees
19 Feb - 20 Feb
Spectacular water view condo!

Lakefront! Amazing Fishing! Arcades, Kayaks, Bikes

9.8 out of 10, Exceptional, (43)
"We were quite comfortable at the The Lake Haus. It was very peaceful looking out at the bay from the firepit area and the sunsets from the dock were gorgeous. The game room was a hit with everyone, especially the golf and Tempest arcade games and the electronic dart board. The bunk room was very well laid out and the beds very comfortable. The kitchen and living room/dining area were a bit small for our group of nine, but we made do without too much trouble. This was a nice place to...
Lakefront! Amazing Fishing! Arcades, Kayaks, Bikes

Beechwood Cottage -Sleeps 4! A-Frame in Sister Bay, WI: Coffee Bar & Fire Pit!

10.0 out of 10, Exceptional, (39)
"My wife and I loved the cottage. It had everything we needed. It is close to Sister Bay but secluded also. We would definately recommend for a couple or small group."
Beechwood Cottage -Sleeps 4! A-Frame in Sister Bay, WI: Coffee Bar & Fire Pit!

Waterfront Dream Cottage With A Million Dollar View, HARBOR Unit

10.0 out of 10, Exceptional, (153)
"My husband and I really enjoyed our stay. The property was as described, tidy and offered great views. The sauna was a nice way to warm up after hiking. "
Waterfront Dream Cottage With A Million Dollar View, HARBOR Unit

Waterfront gem, sandy beach, modern kitchen, large great room, free firewood

10.0 out of 10, Exceptional, (91)
"Absolutely amazing stay! Great location & amenities. Looking forward to coming back in the summer!"
The price is €564
includes taxes & fees
18 Feb - 19 Feb
Waterfront gem, sandy beach, modern kitchen, large great room, free firewood

Sister Bay Vintage Log Cabin

10.0 out of 10, Exceptional, (166)
"We loved this adorable cabin. Most importantly it was sooo clean and they have everything you need. Just bring your clothes and enjoy your getaway "
Sister Bay Vintage Log Cabin

Lakefront!! 5 Star Home on the Bay! Waterfront Property with 200ft of Shoreline.

10.0 out of 10, Exceptional, (121)
"We so appreciate Kurt and Triona for making their property available. It is beautiful inside and out, very spacious, with room for everyone in the family (including our dog!), yet a very private space from neighbors, and we lacked for nothing. Everything we needed for cooking and relaxing. It was an amazing Christmas visit. "
Lakefront!! 5 Star Home on the Bay! Waterfront Property with 200ft of Shoreline.

Cozy Cabin! Dwntwn Fish Crik! Hike, Bike. Dogs ok!

9.4 out of 10, Exceptional, (74)
"The little yellow cottage is situated in the perfect location of Door County! Right on the main drag of Fish Creek, the park and Fish Creek downtown are easily accessible from the cottage. Although it is situated on the main highway, we found little disruption via car noise. The cottage is fully equipped with everything you need for a comfortable stay, including a full kitchen. While small, the cottage offered everything needed for a small family or two couples. Additionally, the cottage...
Cozy Cabin! Dwntwn Fish Crik! Hike, Bike. Dogs ok!
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

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

8.6 out of 10, Excellent, (111)
"Great property within walking distance of anything you would want in Bailey’s Harbor"
Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!

Red Cherry Woods Cottage 🍒 New Construction!

10.0 out of 10, Exceptional, (47)
"Lovely A-frame on wooded lot. Well appointed inside- comfortable and nice bedding. Beautiful view of the woods from the master bedroom. Excellent water pressure in shower. Nice white towels. We had most everything we needed in the kitchen. No complaints. Would definitely stay again! We were on a winter getaway. Will go back when we can enjoy the patio :O) "
Red Cherry Woods Cottage 🍒 New Construction!

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

10.0 out of 10, Exceptional, (232)
"The house is lovely, with all the amenities you need for a quiet time away. Being right on the lake was really nice "
Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!
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.

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?

Waterfront Home In Baileys Harbor ~ Fantastic Views Of The Harbor And Islands!: This highly rated holiday home rental in Baileys Harbor is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Another good choice for your trip to Baileys Harbor is Lake-House With The Best View Of Cana Island And It's Lighthouse You Can Find!.

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.