Holiday houses in Gibraltar

Bay View Beauty on the Bluff

**Stunning home on the Bluff with Spectacular, Panoramic Bay Views** Enjoy the best of Door County at this beautiful 5-bedroom, 4.5-bath home perched on Gibraltar Bluff, offering breathtaking views of Fish Creek Harbor. This spacious retreat sits on over 2 wooded acres and is conveniently located less than 5 minutes from both downtown Fish Creek and the entrance to Peninsula State Park, making it the perfect destination for families or groups looking for an unforgettable Door County experience.

Family · Location · Wi-Fi

Evergreen Hill B Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! All 3 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

Family · Value · Decor

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).

Family · Value · Bathroom

Magical Countryside Home | Hot Tub near Fish Creek

This home is perfect for a family or couples getaway! Spacious 4 bedroom home, situated on a beautiful lot with lots of outdoor space for the whole family to enjoy! You will love the footpath to the secluded fire pit for a magical night under the stars. 3 king bedrooms with en-suite bathrooms, one queen bedroom, a roomy living room and sitting room PLUS an upstairs lofted living room ensures space and privacy for all! Enjoy the cool nights or winter days in the hot tub added in fall of 2025!

Location · Value · Beach

Arbor Cottage Loft

Arbor Cottage LOFT is nestled in the heart of the Village of Ephraim on the shores of Eagle Harbor. The "LOFT" is upstairs/attic of the original/historic cottage (circa 1853) and has been lovingly remodeled into a charming Scandi-inspired LOFT w/ its own private entrance. The LOFT has west-facing views to savor unforgettable sunsets, island & bluff vistas. Enjoy 100' of private lakefront area to swim, kayak, or just relax with a glass of wine and watch a fabulous sunset over Eagle Harbor!

Family · Location · Condition

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.

Family · Location · Parks

Cottage in the Creek- Centrally Located DoCo Oasis

Welcome to the Cottage in the Creek, our family’s home in the heart of Fish Creek. The four of us grew up here and later renovated the cottage to create the kind of Door County getaway we’d want to share with our own families and friends. With four bedrooms, 3.5 baths and plenty of space to gather, it’s an ideal home base for your stay—and best of all, you can leave the car behind. The shops, restaurants, waterfront and charm of Fish Creek are just a short stroll from your front door.

Value · Location · Bathroom

Mid Century Lake House with private beach

Come enjoy Door County in this beautiful lake house. Completely renovated with private beach access this is the perfect place to relax. Everything in this home is brand new! Conveniently located next to Ellison Bay & Sister Bay, enjoy all the hustle and bustle of Door County and retreat back to the serenity of the house Swim in the lake, paddle board, or take one of our bicycles and enjoy the scenery. Enjoy the winter snow shoeing, cross country skiing or snowmobiling.

Value · Location · Backyard

The Glass House on Birch Bluff

The Glass House on Birch Bluff is named in honor of Fredrica “Fritzie” Glass who had it built in 1969. Fritzie was an artist, teacher and author who led a rich life both in Milwaukee and Door County. We’ve tried to honor her love of nature and beauty in this space. The cottage sits atop a private bluff on three gorgeous acres in Fish Creek. It is a wonderful place to be alone and unwind, and yet a short distance to all that Northern Door County has to offer!

Location · Value · Long stay

Door County Lake House

We are excited to introduce our Architect-designed modern lake house in the town of Clay Banks! Enjoy serenity, sweeping views of Lake Michigan from a secluded back deck & expansive windows from every room in the house. Embrace slower living, waterfront amenities, neighborhood park with trails and the magic of lake life. You’ll enjoy water fun for the whole family, huge back deck with dining for 8, an outdoor lounge area, and fire pit near the water.

Location · Family · View

2 Bed A-Frame in Sister Bay, Fire Pit, Coffee Bar

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.

Location · Family · Walkability

4 Bed, Fish Creek, Game Garage, Coffee Bar, Trails

Escape to Orchard Ranch in Fish Creek—a newly remodeled home that sleeps 10 and offers private walking trails, a fire pit, ping pong table, and a cozy coffee bar. Just minutes from Peninsula State Park and Fish Creek dining. Great for families, friend groups, or couples' getaways. Only a few open summer dates remain—book now and save! -7 minutes to Peninsula State Park -2 minutes to Lautenbach's Orchard -5 minutes to Egg Harbor

Family · Location · Accuracy