Photo by ‎Staci Neidert

Holiday Homes in Baileys Harbor

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Featured Holiday Homes in Baileys Harbor

The Cherry Cabana- Sister Bay

10.0 out of 10, Exceptional, (5)
"We stayed here for 5 nights with our family for our daughters wedding at Northern Haus. We had a great time and would definitely stay at The Cherry Cabana again and recommend it to everyone! Loved the main kitchen/living area with loads of seating areas for everyone to be together. The kitchen was very well stocked with everything we needed and more! I appreciated the labeled cupboards and drawers, made it super easy to find everything. The downstairs has a large family room with lots of room on...
The Cherry Cabana- Sister Bay

BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek!

9.0 out of 10, Wonderful, (12)
"Great for large groups with children. Two large living rooms created space for adults and children. Layout was perfect and look forward to staying again. "
BRAND NEW! Newly Constructed home, walking distance to downtown Fish Creek!

Beautiful Door County Waterfront Property - Fall Dates Available

9.8 out of 10, Exceptional, (20)
"The house was clean and comforable. We enjoyed the lovely view of the lake and the open space for making meals and playing games. Will rent this house again for our next trip to Door County. "
Beautiful Door County Waterfront Property - Fall Dates Available

Wild Cedars - Cana Island - Lake Michigan - Amazing new home

10.0 out of 10, Exceptional, (182)
"This is our 2nd stay here! This home is just so beautiful, impeccibly clean, and stocked with all kinds of things for the kids to do. Also, the owners are quick to respond with questions and provided some great dining recommendations. We truly enjoyed our stay and look forward to coming back again."
Wild Cedars - Cana Island - Lake Michigan - Amazing new home

New! Hot Tub, 2 Blocks to SB, Fire Pit Patio, Dogs

2.0 star property
8.8 out of 10, Excellent, (5)
"Perfect stay from start to finish. Hands down one of the nicest rental homes we’ve ever stayed in, and truly a one of a kind in Door County. The location is unbeatable, to have a private home in the woods walking distance to downtown Sister Bay. Very thoughtful amenities in the home made for an effortless stay, like the Bluetooth speakers, chargers, games, and the pack n play and kids toys. We will definitely be back!"
New! Hot Tub, 2 Blocks to SB, Fire Pit Patio, Dogs

NEW! A truly pretty, spacious home - for 1 or 2 couples, or a small family.

10.0 out of 10, Exceptional, (54)
"The property is amazing and the host, Colin is great. Can’t wait to return in spring when all the flora is in full bloom. "
The price is AU$791
includes taxes & fees
11 Dec - 12 Dec
NEW! A truly pretty, spacious home - for 1 or 2 couples, or a small family.

Harbor School House - Private home, great outdoor space, 5 minute walk downtown

10.0 out of 10, Exceptional, (11)
"We were celebrating my daughter and my birthday. We love Door County during the fall! Had a great stay in your beautiful home! LOVED the fireplace. Will definitely return and hope to rent your home again❤️"
Harbor School House - Private home, great outdoor space, 5 minute walk downtown

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! "
The price is AU$897
includes taxes & fees
26 Dec - 27 Dec
Downtown Sturg - Arcades/Theater/Modern

NEW! "Spruce Retreat" is a beautiful and romantic hideway.

10.0 out of 10, Exceptional, (38)
"We had an amazing time 🤗"
NEW! "Spruce Retreat" is a beautiful and romantic hideway.

Lake Michigan Beach Home with Over 100’ of Private Sand Beach! Pets Welcome!

10.0 out of 10, Exceptional, (213)
"What a wonderful time. This home provided everything we could have needed and more. Great spaces to spread out, all the kitchen equipment for making fun meals, excellent WiFi, bright outdoor lighting, ample parking space, and excellent homeowner communication with all instructions! Thank you Ted for making our weekend truly special. "
Lake Michigan Beach Home with Over 100’ of Private Sand Beach! Pets Welcome!

Northern Lights Farmhouse with Hot Tub

10.0 out of 10, Exceptional, (24)
"My sisters and i stayed here with some of our hubbies. It was perfect. The place is stunning and easily accommodated our group of eight. It had many little touches to make our stay special. . We loved taking morning walks around the large property and sitting around the fire pit at night. It was the perfect get away . "
Northern Lights Farmhouse with Hot Tub

Heart of Fish Creek!- Newer Construction - 4BR, 4.5BA Condo-Sleeps 8-10

9.6 out of 10, Exceptional, (190)
"There were 9 of us girls that came to Door County for a four day weekend. The location was perfect and the house was absolutely beautiful! Thank you for helping make it memorable. We will definitely be back. "
Heart of Fish Creek!- Newer Construction - 4BR, 4.5BA Condo-Sleeps 8-10

Harbor House located in the heart of Ephraim

10.0 out of 10, Exceptional, (177)
"Love this house! Cozy, clean, and lots of Door County charm with the large, enclosed front porch. (The porch would be ideal for a family game night in the summer with its tables and porch swing.) We had a nice time at the fire pit surrounded by plenty of Adirondack chairs for our group. (Bring your own firewood.) Even saw beautiful northern lights from the beach a couple of blocks away, and heard coyotes yipping and howling in the wooded area to the west. Very responsive host. Highly recommend!"
Harbor House located in the heart of Ephraim

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!

Large Home with Ideal Central Sister Bay Location!

9.8 out of 10, Exceptional, (27)
"The house worked well for our group of 8. There were a few things that could have been kept up on. Toilet in downstairs bathroom loose and wobbles under you. Shower head looked like it was falling off in downstairs bathroom. All 3 bathroom vents caked with dust (we cleaned them). Keurig still didn’t work after another guest previously stated broken. Coffee maker itself was pretty gross looking and has seen better days. Fireplace inoperative. Certain lights throughout house don’t work (living...
Large Home with Ideal Central Sister Bay Location!

Boutique Home in Door County w/ Eagle Harbor Views

10.0 out of 10, Exceptional, (59)
"The home is clean, comfortable and has a beautiful view of the water. We enjoyed staying here and wouldn’t change a thing. "
Boutique Home in Door County w/ Eagle Harbor Views

NEW Five Bedrooms with Ensuite Bathrooms that Sleeps 24 with Outdoor Hot Tub

10.0 out of 10, Exceptional, (7)
"My family and I really enjoyed our stay! The house was very clean and stocked with the basics to survive a weekend. They had paper products as well as cleaning essentials like laundry detergent, dish soap etc. the management team was very responsive and made check in a breeze. We were located close enough to the town but also enjoyed the rural environment and were surrounded by woods. My kids loved the game garage and spent a lot of the house time out there. Every room has its own bathroom...
NEW Five Bedrooms with Ensuite Bathrooms that Sleeps 24 with Outdoor Hot Tub

Enjoy 110' of Waterfront w/ Water Toys at Sandy Bottom Bay Beach House For 8!!

9.8 out of 10, Exceptional, (13)
"My wife and I stayed to celebrate our 33rd wedding anniversary. We wanted a place close to both Green Bay and Door County. The house was perfect for us. Clean and bright with the sun streaming in each morning. The leaves were stunning on the two mile loop for quiet walks at any time of day. We would love to stay again and would bring our family next time to enjoy the activities on and off the water."
Enjoy 110' of Waterfront w/ Water Toys at Sandy Bottom Bay Beach House For 8!!

Sister Bay Vintage Log Cabin - Recent Remodel

10.0 out of 10, Exceptional, (162)
"Perfect location, abt 1/2 mile from sister bay restaurants and shops. View of water. Clean, cozy and super cute!! "
Sister Bay Vintage Log Cabin - Recent Remodel

Perfect For Family Reunions/Weekend Getaways/Large Groups. A hidden oasis!

9.4 out of 10, Exceptional, (129)
"Our family stayed for family wedding. We were busy and sorry we couldn’t spend more time enjoying the beautiful setting."
Perfect For Family Reunions/Weekend Getaways/Large Groups. A hidden oasis!
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 property types 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
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

Black Friday: Members save 30%+

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