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Baileys Harbor vacation rentals

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Top-rated vacation rentals in Baileys Harbor

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Barn in Sister Bay

4.84 out of 5 average rating, 147 reviews

Three Sister's Cottage Barn Retreat

Enjoy a carefree stay in our private, one of a kind reconditioned barn with stone patio. The original 4x4's structure and push out casement windows ground the renewal of this sweet dwelling. A travertine stone floor, cherry live edge and soap stone countertops make the custom built kitchen w/ island seating easy to sink into. The glass shower with view of the meadow and an entire 2nd floor master bedroom with tub for two support you to settle and relax into the northern door peninsula's bliss.

Rental unit in Fish Creek

4.99 out of 5 average rating, 238 reviews

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).

Home in Baileys Harbor

4.93 out of 5 average rating, 238 reviews

Waterfront on Peaceful Moonlight Bay

Contact us for reduced offseason rates per # of guests! 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).

Cabin in Ellison Bay

4.91 out of 5 average rating, 118 reviews

Unique architect-designed home on waterfront bluff

An architect gem with a million dollar view. Located on a private drive near Ellison Bay, this home is 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 space is ideal for older children to have their own space.

Home in Baileys Harbor

4.99 out of 5 average rating, 158 reviews

Winding Down - A Retreat on the "Quiet Side"

Winter is coming and there's still time to book your getaway. Enjoy the season and get ready to relax and recharge with family & friends. Winding Down is the perfect place to enjoy the quiet side of DC. We are walking distance from the Nature Preserve & the shores of North Bay. Located in a beautiful cedar forest that provides a needed respite. Plenty of privacy but also a short drive to Ephraim & Sister Bay. Venture out for a hike or take out the snow shoes when the snow starts to fall.

Guesthouse in Fish Creek

4.97 out of 5 average rating, 194 reviews

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.

Cottage in Baileys Harbor

4.95 out of 5 average rating, 111 reviews

Coffee Bar, Fireplace, Winter Discount—Sleeps 8!

Pull off the highway and relax in our century-old cottage. Stonewall Cottage is located on almost three private acres and features tongue and groove pine walls, original hardwood floors, vaulted ceilings, decorated with a warm mid-century modern charm and is equipped with everything needed for a relaxing stay. Be close to it all! Only a short 2 minute drive to downtown Baileys Harbor, 10 minute drive to Peninsula State Park and 10 minutes from everything Sister Bay has to offer.

Condo in Ephraim

4.94 out of 5 average rating, 237 reviews

Bright • Cozy • Clean • Condo Near Water • Ephraim

Our bright, clean, cozy, ground-floor condo is just a block from the water in Ephraim. There is 1 bedroom (queen) and a sleeper sofa in the living space (queen). There is a spacious bathroom with shower/tub and large vanity. Shower and toilet area are separate from sink/vanity area. Walk right out onto your own private patio which connects to our spacious yard. Full kitchen w/ stove (small oven/stove), fridge, microwave, toaster, Keurig, cookware, dishes, glassware & dishwasher.

Home in Baileys Harbor

4.91 out of 5 average rating, 309 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

Cottage in Sister Bay

4.98 out of 5 average rating, 100 reviews

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.

Home in Baileys Harbor

4.96 out of 5 average rating, 245 reviews

Baileys Harbor Yellow Home with a View

Situated in the heart of down town Baileys Harbor, Wisconsin. You can sit in the kitchen and see Lake Michigan as you drink your morning coffee. No need to drive if you do not want to, you have restaurants, bars and shops all within walking distance. You have the whole house to yourself, but we own a coffee shop one building over, in case you need anything. The house is a late 1920's house, but newly upgraded, with a new kitchen and bathroom.

Home in Sturgeon Bay

4.98 out of 5 average rating, 223 reviews

Lily Pad Cottage, Door County: Waterfront Cottage

Lily Pad is perched, on the waters of Sturgeon Bay, with a historic shipbuilding waterfront and artistic culture. A perfect romantic getaway for a couple seeking quality time in one of the last cottages on the waterfront of Sturgeon Bay. Fantastic location, close to everything on the west side of the city. Lily Pad has a deck and a fire pit in the yard! Need more space?, Eagle View Suite is a two bedroom, next door to Lily Pad Cottage.

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Popular amenities for Baileys Harbor vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Baileys Harbor's top sights

Door County Brewing Co. Taproom and Music Hall49 locals recommend

Chives Door County26 locals recommend

Bearded Heart Coffee25 locals recommend

The Ridges Sanctuary17 locals recommend

Baileys Harbor Cornerstone Pub16 locals recommend

Harbor Fish Market & Grille15 locals recommend

Other great vacation rentals in Baileys Harbor

Serviced apartment in Fish Creek

4.87 out of 5 average rating, 60 reviews

1 Bedroom Suite in a World-Class Swedish Resort

Cabin in Sister Bay

4.98 out of 5 average rating, 80 reviews

3 Bed, 2 bath log cabin in Sister Bay w/ fire pit

Home in Baileys Harbor

5 out of 5 average rating, 23 reviews

Luxury Waterfront Kangaroo Lake

Home in Sturgeon Bay

4.93 out of 5 average rating, 41 reviews

The Cute Yellow House Walkable to Downtown

Home in Sister Bay

5 out of 5 average rating, 30 reviews

The Aqua Door Escape

Cabin in Sister Bay

4.98 out of 5 average rating, 96 reviews

Blue Moon Cabin

Home in Baileys Harbor

4.97 out of 5 average rating, 65 reviews

Quiet 3 bedroom wooded home in Baileys Harbor

Cabin in Egg Harbor

5 out of 5 average rating, 27 reviews

Luxury A-Frame w/Sauna & Lake Access

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