Holiday rentals in Sister Bay

4.97 out of 5 average rating, 35 reviews

Apartment in Sister Bay

Sister Bay Gem-steps to the beach and downtown!

New, luxurious, fully furnished Condo located in the heart of downtown Sister Bay with water views and directly across from the Sister Bay Beach. 2 bedrooms with queen sized beds and private bathrooms with tiled showers, full-sized kitchen with granite countertops, stainless steel appliances, 55" TV, washer/dryer, fireplace and attached garage will ensure a visit that will make return visits something you will want to do regularly. The couch also reclines for additional sleeping area and High Speed Spectrum Broadband Service available to accommodate your streaming services. There is no better place to stay while visiting Door County and all that it offers. Sister Bay boasts attractions such as the goats at Al Johnson’s, local coffee shops, casual and fine dining, browsing the many shops & galleries or just enjoying the view from the beach across the street. If you want to stay in and relax, the in-unit fireplace welcomes you to snuggle in for the day and enjoy a peaceful time together. Whether you are here for a quick getaway, weeklong vacation or a festival, Beach View Condos is your place for a stress free destination. Great place for 2 couples or a family. **Check with host for additional condos to reserve if your group is larger. **This is a townhome design that includes 2 sets of stairs-not handicap accessible

Place to stay in Sister Bay

4.86 out of 5 average rating, 21 reviews

Cottage on SisterBay Inn grounds

Relax at this peaceful and unique place to stay. Just a half mile away from downtown beautiful Sister Bay Located on Sister Bay Inn grounds including outdoor heated pool (May24-Sep5) hot tub, firepit, fitness room and basic continental breakfast! King studio sweet (all open space) gives you privacy tucked away by the meadows while enjoying all Sister Bay Inn amenities. To access the cabin, you are required to walk down the full flight (15) stairs from the parking lot. We do not have an elevator

5 out of 5 average rating, 5 reviews

Apartment in Sister Bay

Prime location, professionally desgined with view

With over four years of hosting experience, we are thrilled to join the Airbnb community and introduce our latest property. Bleu on 2 is a stunning vacation rental in Sister Bay, where luxury meets modern comfort. Garnering nothing but 5-star reviews, totaling 43 so far (different platforms), our property exudes sheer elegance and local charm, providing the perfect backdrop for an unforgettable getaway. Embrace the breathtaking bluff of Sister Bay and experience the best of Door County with us.

4.88 out of 5 average rating, 42 reviews

Cottage in Sister Bay

Birchwood Cottage, Private Retreat w/short walk DT

Welcome to your own private getaway in the heart of Sister Bay, Birchwood Cottage (RT-364). This newly renovated cottage is nestled in a lot of mature Cedar trees. Sit on the private front porch/patio & relax in calm, dappled sunlight while listening to the birdsong. Inside, enjoy the new, fully equipped kitchen, bath & comfortable bedroom/living room area and a full kitchen table for dining and games. This location also offers you the best of both worlds due to it's .5 mile walk downtown.

4.98 out of 5 average rating, 252 reviews

Flat 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).

5 out of 5 average rating, 102 reviews

Apartment in Sister Bay

101 | Luxury | Downtown Sister Bay | Door County

Owner operated + private entrance + no shared spaces + CDC cleaning standards. Rare opportunity to rent the developer’s unit in Sister Bay’s newest, luxury, marina view condominium development! Custom cabinetry, quartz countertops, stainless steel appliances, garage parking, and more await you in this dedicated vacation rental. Walk out your patio door to 14 plus restaurants, bars, and coffee shops, including the famous Al Johnson’s. Virtual tour in highlights on IG "@101sisterbay"

4.89 out of 5 average rating, 131 reviews

Hot Tub & Game Room, Walk to Marina, Pets welcome

Scandia by Getaway and Stay Enjoy the best of Sister Bay in this secluded retreat, just 5 minutes from the marina! The spacious backyard is perfect for kids and dogs, featuring a brand-new 5-seater hot tub, a cozy firepit, and a grill for starry nights. Inside, two sunlit living rooms offer plenty of space to unwind and make lasting memories. Whether you're seeking outdoor adventures or cozy nights in, this home is your perfect getaway. Book now and experience the charm of Door County!

4.94 out of 5 average rating, 17 reviews

Modern Home w/ Hot Tub, Games & Best Location

Wooded Wonder by Getaway and Stay Just 2 blocks from the harbor and 4 blocks from Al Johnson’s, this spacious, light-filled home in Sister Bay offers a unique vacation experience. This home features an open kitchen and living area perfect for gatherings. Have fun with the foosball table and arcade games, or unwind in the lush yard with a fire table and scenic forest views. Whether you're looking for relaxation or adventure, Wooded Wonder combines the best of both in an ideal location.

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, 129 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.

5 out of 5 average rating, 117 reviews

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!

4.95 out of 5 average rating, 107 reviews

Cabin in Sister Bay

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

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sister Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sister Bay

4.98 out of 5 average rating, 42 reviews

Sister Bay 3BR Cottage - Cozy, Central Location

LynnRating, 5 stars3 days ago

We had great family time! The home was very clean and loved the mid century vibe. Everything we needed for a relaxing stay, well equipped. Enough space, with a separate bedroom and bath upstairs, along with a loft for extra hanging out space. Plenty of space for family of four with two older teenagers. It’s a quiet and peaceful location, but can walk to town if looking for things to do. We would return!

4.9 out of 5 average rating, 10 reviews

Home in Sturgeon Bay

Cliff Cottage - Tranquil views

JenniferRating, 5 stars2 weeks ago

We absolutely loved our stay at Cliff Cottage! Everything was clean and well kept, there were lots of amenities, and the host was very responsive. Water access would have been nice, but we found plenty of other beaches nearby. We also loved the location: close enough to walk to things in Jacksonport or ride bikes to Cave Point County Park. It was serene, relaxing, and just what we were looking for! We will definitely look to stay here again the next time we visit Door County.

4.96 out of 5 average rating, 26 reviews

Cabin in Sister Bay

Waterfront A-frame: Vintage Charm, Modern Comfort

KateRating, 5 stars2 months ago

Such a beautiful cabin on a protected bay of Lake Michigan but still see enough to feel the big water and hear the waves crashing. Awesome fire place great place to sit and read and relax by the fire. Lots to do nearby, if you want to leave. The hosts are excellent and welcoming. Would love to go back! Pet friendly is a plus.

Flat in Sister Bay

4.67 out of 5 average rating, 205 reviews

The Yoga Pad - Open & Eclectic

MohdRating, 5 stars3 weeks ago

The stay overall was good and the space itself was clean and comfortable. Brad was helpful and responsive throughout. One thing I didn’t know before booking this unit is part of an existing house and there are three interior doors connecting to other parts of the home, including one that leads to someone’s porch. While all the doors were locked, they aren’t fully walled off, which raised some privacy concerns for me. The first night, I felt a bit scared and uneasy with thoughts like “what if someone walks in?” Since I wasn’t aware of this setup beforehand, I couldn’t cancel the stay. But over time, I got used to it and reminded myself everything was secure. If you’re okay with this kind of shared structure and locked but not sealed-off doors, it’s still a nice place to stay. Thanks, Brad, for hosting. ⸻ Let me know if you want to tone it down or make it even more straightforward.

5 out of 5 average rating, 14 reviews

w/ Hot tub - Luxury home in Sister Bay +Groups!

MollyRating, 5 stars4 months ago

Immaculate home with responsive owner team! Spent a winter weekend here with a big group of friends. It was wonderful having 4 beds and 4 bath for privacy. Couldn’t have enjoyed the stay better! We ran into a few issues with the TV not working, and they responded right away. Highly recommend.

5 out of 5 average rating, 20 reviews

The Sister Bay Haus

KarlaRating, 5 stars1 month ago

My friends and I absolutely loved our stay at Sister Bay Haus. Gorgeous home that felt cozy and elegant at the same time. Great amenities. Close to places we wanted to visit. The hosts are wonderful! I highly recommend a stay here!

5 out of 5 average rating, 6 reviews

#1 Downtown Location! Hot Tub, Dogs

SaiRating, 5 stars1 month ago

We had a fantastic stay. The house is incredibly comfortable and ideally located - just a few blocks from great restaurants, shops and the waterfront. We really appreciated all the thoughtful touches, like a fully stocked kitchen and super cozy beds. The hot tub was an amazing bonus after long ays out and about. It's clear that the hosts genuinely care about creating a great guest experience. Will definitely return for a future stay next year! Highly recommended!