House vacation rentals in Sister Bay

A spacious home is nestled amid tall trees, featuring a light gray exterior and a prominent gabled roof. Large windows allow for natural light, while a wraparound deck with railing offers outdoor space. The driveway leads to the side of the property, creating a welcoming entrance.

5 out of 5 average rating, 4 reviews

Group-Retreat • Firepit, Deck, Near Beach & Shops

Bay Dreaming is the ultimate retreat for families and friends, located just under a mile from the beach and the heart of downtown Sister Bay. This spacious home comfortably sleeps 12+ and features three private wings, each with its own full bathroom—providing plenty of comfort, space, and privacy for everyone. Enjoy the fenced backyard with lawn games, a large firepit, and plenty of room to relax. Dine al fresco or unwind on the wraparound deck nestled on a peaceful, wooded half-acre lot.

The open-concept kitchen and dining area features green cabinetry and stainless steel appliances. A round braided rug is placed under the dining table, surrounded by modern chairs. Natural light fills the space, highlighting the adjacent living area with comfortable seating and decorative accents.

4.91 out of 5 average rating, 106 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.

The charming home, surrounded by lush greenery, features a wide front porch and well-maintained landscaping. A serene backyard with outdoor seating invites relaxation, complemented by the peaceful natural setting that enhances the sense of seclusion.

4.87 out of 5 average rating, 135 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!

A bright living area features wooden beams and a cozy seating arrangement. A plush sectional and two upholstered chairs are centered around a coffee table, while a large artwork and a wall clock add character to the space. Natural light fills the room through two windows.

4.87 out of 5 average rating, 112 reviews

1900s renovated Farmhouse with spacious yard

Welcome to The Little White Farmhouse! This newly renovated 1900s farmhouse is conveniently nestled between the hustle and bustle of downtown Sister Bay and Ephraim’s picturesque sunsets. Many updates throughout, all while maintaining the character and history of the home. Take advantage of our one acre yard, deck with gas grill, and fire pit area for all of your outdoor entertaining and relaxing. We are centrally located - just minutes from anything that Door County has to offer!

A private outdoor space is depicted featuring a pergola over a circular stone fire pit area. Surrounding greenery provides a natural backdrop, while patio seating is arranged nearby, inviting relaxation in a serene environment.

4.91 out of 5 average rating, 105 reviews

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)

A spacious wooden deck overlooks the tranquil waters of Lake Michigan, featuring a round table surrounded by black metal chairs. Long benches line the edges, offering additional seating. Lush greenery can be seen along the shoreline, enhancing the serene atmosphere.

4.91 out of 5 average rating, 330 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

The entrance features a bright red door set against a gray wooden wall. A small window with white trim is visible nearby. A snow shovel, a bucket, and two wooden sleds are arranged neatly next to the door, along with a cozy blanket and a pair of boots.

4.88 out of 5 average rating, 275 reviews

Sister Bay Eclectic Cottage

Stunning fresh + modern cottage ready for your visit NEW as of August 2018! Less than 1 mile walk or drive to Sister Bay Downtown + just minutes from the Beach! 3 Bedrooms: 1 king w/ on-suite bath, 1 queen w/ on-suite bath, twin trundle bed 3 full bathrooms: 1 on the main floor, 2 on-suite on 2nd floor Great cooks kitchen, fully stocked w/ open concept living space, w/ Sonos in kitchen! BBQ gas grille + awesome fire pit, expansive deck w/ dining space & lounge chairs

Top guest favorite

The exterior of a charming farmhouse features a covered porch with two green folding chairs beside a welcoming front door. Lush greenery and flower beds enhance the home's inviting atmosphere, accompanied by a view of a small storage shed.

5 out of 5 average rating, 9 reviews

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.

Top guest favorite

The exterior of a freshly remodeled home is displayed, featuring a dark blue facade with white trim. A large screened-in porch wraps around the front, complemented by plentiful windows. The surrounding area is wooded, offering a natural, serene environment.

Home in Fish Creek

4.97 out of 5 average rating, 148 reviews

Maple Grove Landing (Brand New Rental)

Beautiful Home freshly remodeled in the heart of northern Door County with roughly 2600 sqf. Outstanding location!!! Located within walking distance to Peninsula State Park and Golf Course (between Ephraim and Fish Creek). The home features three full bedrooms and a bunk room. There are two full baths and one-half bath, washer and dryer, beautiful full kitchen, high speed wireless internet, cable television, and a large wrap-around screened-in porch.

A cozy living area features a comfortable blue sofa with decorative pillows and a light-colored accent chair. A wooden coffee table sits in the center, while large windows offer views of the outdoors. A television is positioned on a console table, enhancing the inviting space.

4.9 out of 5 average rating, 109 reviews

Family Friendly Retreat in the Heart of Sister Bay

Our charming, Swedish-style chalet is located on the main drag, on the north side of Sister Bay. You and your group will love walking into town for a trip to the beach and park or a meal at any of Sister Bay's fine restaurants and coffee shops. Or just relax on our front deck and read a book, enjoy a beverage and watch the busy hustle and bustle of Door County. Our cottage is perfect for couples, families (with kids) and people traveling with pets.

An open-concept living space is highlighted by a high ceiling with wooden beams. Large windows frame views of the outdoors, and a spacious sectional sofa is arranged around a coffee table atop a patterned rug. Light wood flooring complements the overall design.

4.94 out of 5 average rating, 262 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).

Top guest favorite

A cozy living room features a light grey couch adorned with navy blue pillows, paired with two beige armchairs. A round wooden coffee table is centered on a soft area rug, while large windows provide natural light and views of the surrounding greenery.