Holiday rentals in Sister Bay

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.

Above Bakery: Cozy Studio, Perfect for Couples!

Bird's Nest by Getaway and Stay This charming second-floor studio offers a peaceful retreat just minutes from downtown Sister Bay. Enjoy a private entrance and a spacious balcony, perfect for morning coffee or sunset views. Located above Cultured, a beloved sourdough bakery, you’ll wake up to the aroma of freshly baked bread, and while our bakers start early, a noise machine ensures a peaceful rest. Experience the warmth of a bakery-side stay—book your Door County getaway today!

Maple Cottage, Cute & Cozy, steps to downtown.

Very cute and cozy home to enjoy Door County from. Large, private back yard with pergola and plenty of patio seating including a fire pit area. Charcoal grill on site. Home is centrally located between Washington Island and Egg Harbor. It's within .4 mile walking distance to downtown Sister Bay. Great place to get away and relax and still have the fun of the restaurants and shops nearby. This is our home away from home and we hope it will be yours too. (Maple Cottage RT-364)

The Key to Happiness

Sleeping 4-6 between 4 beds, Plum Retreat provides a one-of-a-kind Door County experience. With 2 large bedrooms (plus giant living room with queen sofa bed, dining area and full kitchen), the 1700 sq-feet have a charming cottage-like feel. Conveniently located with gorgeous perennial gardens, it makes a romantic, peaceful or fun space. Private lawn & patio/grill. Pretty much everything has been thought of. Last summer, all 37 groups of people gave it a 5-star rating!

Chicory Hill: All Ensuites, Game Rm & Fireplace!

Experience a higher standard of vacationing and unparalleled attention to detail at Chicory Hill, a newly remodeled luxury vacation home in Sister Bay. Whether you are friends coming together to celebrate a long-lasting bond, or a family uniting across generations to create unforgettable moments, we offer the ideal vacation retreat for meaningful connection. Chicory Hill has every ingredient necessary to make authentic and enduring Door County vacation memories.

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.

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!

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

Door County at its finest! Located minutes away from Sister Bay's main attractions. You can enjoy the privacy of the cabin a wooded lot with quick access to many activities in the surrounding area. 1 mile away from Northern Haus wedding venue 10 minutes drive from Peninsula State Park 20 minutes drive from Newport State Park 25 min from Whitefish Dunes State Park 20 min from ferry to Washington Island

Luxury Loft Retreat- Walkable Downtown Vibes!

Welcome to your perfect getaway in the heart of downtown Sister Bay! This newly built, luxurious condo offers a premier short-term rental experience that you won't find anywhere else. With a prime location and direct access to the stunning Sister Bay Beach just steps away, this is the ultimate destination for relaxation and exploration. *Roll away bed available in condo*