Holiday houses in Cana Island

4.98 out of 5 average rating, 251 reviews

Apartment in Fish Creek

Night Cap Studio Loft in Downtown Fish Creek

In the heart of Fish Creek, above our bustling Hat Head shop, enjoy your stay in our newly remodeled second story studio loft. Complete with studio bedroom, bath, kitchen with new appliances, sitting room, and private balcony deck. Enjoy walking distance to the beach, shops, restaurants, Peninsula State Park, and more. Close to the action, yet a great hideaway for privacy and relaxation. Bright and cheery, modern, simply stated, and clean. For adult single or couple. (Sorry no pets or kids).

4.9 out of 5 average rating, 102 reviews

Cozy & Relaxing Wooded Home; Close to Everything!

Relax with the family at this quiet, spacious, and secluded 3 bedroom, 1.5 bath home. Just up the road from Lake Michigan and charming downtown Bailey's Harbor, our central location makes it a breeze to visit all of Door County - Sister Bay, Fish Creek, and Ephraim are all just minutes away. Hikers will enjoy the nearby Ridges Sanctuary, Toft Point, and more. This property allows for proximity to all of the fun, while allowing a tranquil and quiet place to stay and relax while on vacation.

4.91 out of 5 average rating, 120 reviews

Cabin in Ellison Bay

Unique architect-designed home on waterfront bluff

An architect gem with a million dollar view. Located on the bay on a private drive near Ellison Bay, it’s close enough to town but far enough away to be secluded. The main house features a roomy living area with sleeper, kitchen, dining room, shower bath, and loft bedroom. The newly-finished "Garage-Mahal" features a full bathroom, two bedrooms (one full and two twins), kitchenette, and small living room with sleeper. This separate building is ideal for anyone who likes their own space.

4.97 out of 5 average rating, 227 reviews

Guesthouse in Fish Creek

Vintage Mod Cottage with fireplace & soaking tub!

Grandview Farm Cottage is a circa 1920s newly renovated, 420 sq. ft. private guesthouse on the grounds of a 2.5 acre Door County property built in the late 1800s. Modern, industrial and repurposed style meets vintage farmhouse charm. Central location allows for quick drive or even a bike ride to either coast of the peninsula. Enjoy nature, wildlife, your own organically grown gardens, and dark starry night skies, while being only 3 miles to nightlife and shopping and beaches and parks.

Farm stay in Baileys Harbor

4.95 out of 5 average rating, 232 reviews

A True Farmhouse Experience

How would you like to get away from it all? How would you like to just kick back, relax, and take things in like the good ‘ol days? The Farmhouse might just be the place for you. Located just outside the town of Baileys Harbor, the Farmhouse is located on Gray-Aire Farms, a working farm since 1960. Nestled in the gorgeous surroundings of Northern Door County, you’ll be able to kick your feet up and take in the fresh country air, while watching the cows graze in the pasture.

4.91 out of 5 average rating, 328 reviews

Never Want to Leave Cottage

Three bedroom, lake home on the shores of Lake Michigan. Step into a beautiful, comfortable, clean environment on quiet North Bay in Door County, Wisconsin. As hosts, we have always taken great care to provide a safe and clean environment for our guests. To protect our guests, we are following the cleaning and sanitizing guidelines based on recommendations from the Centers for Disease Control and Prevention (CDC). We look forward to hosting you! Permit Number: 32-56-1996-00

5 out of 5 average rating, 189 reviews

Cottage in Sister Bay

Cozy A-Frame - Coffee Bar, Fireplace - Sleeps 4!

Trade the hustle and bustle for peace and quiet at our cozy retreat, just 5 minutes from the heart of Sister Bay. Tucked away on 1.6 acres of serene woods filled with beautiful beech trees, the cottage is your perfect getaway spot. Kick back on the spacious front deck, unwind on the screened-in porch, and soak in the natural beauty all around. Inside, mid-century modern vibes meet cozy comforts, with everything you need for a relaxing, stress-free stay.

4.98 out of 5 average rating, 128 reviews

Cottage in Sister Bay

Lofted Pines Cottage

Settle in at Lofted Pines Cottage for your Door County stay! Located off the beaten path, but only a few minutes from downtown Sister Bay or Lake Michigan, Lofted Pines is elegantly situated among mature cedar and fir trees, yet open and airy. Whether you're relaxing on the wrap around porch, cozied up in front of the fireplace or enjoying the wood burning fire pit, Lofted Pines is the perfect spot to unwind after exploring the Door County Peninsula.

4.94 out of 5 average rating, 256 reviews

Waterfront on Peaceful Moonlight Bay

Located on the shore of Moonlight Bay Lake Michigan overlooking Toft and Bues Points. Private waterfront access with beach and dock. Kayaking, canoeing, SUPs, biking, swimming, and fishing (all included). Located on a bike route near Bues Point public boat ramp, Cana Island Light House, The Ridges Sanctuary, and Baileys Harbor. Conveniently located yet private a short trip to Fish Creek/Egg Harbor (15 min), Ephraim/Sister Bay (10 min).

5 out of 5 average rating, 116 reviews

Home in Sister Bay

Cottage in Sister Bay

Beautiful + modern cottage ready for your visit! Cozy up in this private cottage during your Door County stay! Just three miles from downtown Sister Bay, Pineview Cottage is located on a serene lot nestled in the woods. A perfect place for you to unwind after your Door County adventures. If you would rather stay back, relax on our beautiful covered front and back porch or gather around the campfire with friends and family!

4.97 out of 5 average rating, 150 reviews

Cabin in Egg Harbor

The Cabin at Shady Grove

Set among five acres of mature and private woods, this newly renovated vintage log home has 2 bedrooms, 2.5 baths, and sleeps five guests. The property is completely secluded and private, yet only a five minute drive to town and the beach. Relax and unplug. Reconnect with your family, friends, and nature. Welcome to the cabin at Shady Grove.

4.97 out of 5 average rating, 325 reviews

Apartment in Egg Harbor

Award Winning Modern Flat in Egg Harbor - #102

Perfect for couples looking to unwind, recharge, and create lasting memories, The Flats on Church Street offer a warm and welcoming space that feels like home. Come experience the ideal blend of modern design, cozy amenities, and a prime location for your romantic winter retreat.

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Other great holiday rentals in Cana Island

Superhost

Tiny home in Stephenson

4.88 out of 5 average rating, 72 reviews

Natureside A-Frame Cabin: Cozy.Sauna.Hot Tub

KameronRating, 5 stars2 weeks ago

Our stay was absolutely amazing! My new husband, our dog and I came here for our mini moon/ escape after our wedding and exactly what we needed with such a beautiful view. We really appreciated having all of the property questions answered before even needing it such as how to work the sauna and how to actually find the property. We fully plan on coming back here for anniversary’s. 😊

5 out of 5 average rating, 49 reviews

Lakefront cottage w/ sand beach & waterfront deck

DeborahRating, 5 stars1 week ago

Dan & Beth said they wanted us to feel at home and we certainly did! We had 7 adults in our group & we talked about the house & cost to stay there. We all agreed it was absolutely worth every cent. Dan couldn’t have been more helpful whenever we reached out with a question. Being right on the beach was magical. Fires at night with a plentiful supply of dry wood was a nice surprise! Anything you could possibly think of was at our disposal! Even the refrigerator was pristine, which in my experience, doesn’t always happen in a rental. We will miss Sandvik house!

4.98 out of 5 average rating, 42 reviews

Home in Ephraim

The Ephraim House

BaileeRating, 5 stars2 weeks ago

Staying at John & Erin's was a perfect fit for my bachelorette weekend! We had everything we could need, and Erin was great at communicating. They were flexible and able to accommodate an early check-in and late check-out for us too! Overall lovely stay. 10/10 would stay again.

4.92 out of 5 average rating, 24 reviews

Cabin in Fish Creek

Cozy Northern Door A-frame Getaway

JocelynRating, 5 stars1 week ago

This is a great location - within 8-15 mins of Fish Creek, Ephraim and Sister Bay. Quiet, tidy and reasonably priced, especially considering how pricey Door County has become in the last few years. Jacob is very communicative and responsive too!

4.98 out of 5 average rating, 53 reviews

Home in Menominee

Beachfront, Stunning Views, Hot Tub, BBQ, & Games

ApoorvaRating, 5 stars3 weeks ago

This place is beyond breathtaking and worth every penny. Not only is it a dog-friendly haven, the privacy, serenity and accessibility to the beach and sunset views is unbeatable. I highly recommend to disconnect, be present and enjoy the place - no need to leave the house. The host has plenty of in-house amenities, stocked kitchen, and a fenced in yard. We are so excited to return to this cozy cottage soon!

Superhost

Cabin in Baileys Harbor

4.71 out of 5 average rating, 255 reviews

Baileys Harbor Cabin Near Kangaroo Lake-South Unit

KarenRating, 5 stars1 week ago

What a wonderful stay! We were able to relax and recharge. Such a cozy and comfortable place to stay. We’ve stayed at both North and South side now and they pretty much mirror each other. The South yard is a little more private away from the driveway. The Coyote Roadhouse across the street has wonderful food! Alyssa was wonderful to work with. This is the second time we have stayed here and we plan on it again next spring!

5 out of 5 average rating, 8 reviews

Home in Fish Creek

Alma at Loma Cottages

DiannaRating, 5 stars1 month ago

Our stay at the Alma cottage was even better than we expected! The minimal yet thoughtful design boasted large windows that really let the surrounding landscape in allowing for a peaceful ambiance throughout the cabin. The beds were comfortable and we felt at home. Everything was wonderful. We will be back!