Four red Adirondack chairs facing a beach with clear blue water and a grassy foreground.

Sister Bay Holiday Rentals

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Our top choices for Sister Bay holiday rentals

1. Scandinavian Lodge

Scandinavian Lodge
3.5 star property
Sister Bay
9.4 out of 10, Exceptional, (1,729 reviews)
"Wonderful staff and very clean resort!"
United States
Shannon
The price is NZ$237
includes taxes & fees
8 Nov - 9 Nov
Scandinavian Lodge

2. CONDO 3-Sister Bay Serenity-Luxurious downtown condo!

CONDO 3-Sister Bay Serenity-Luxurious downtown condo!
Sister Bay
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful condo located perfectly in the downtown of Sister Bay."
United States
John H.
The price is NZ$736
includes taxes & fees
8 Nov - 9 Nov
CONDO 3-Sister Bay Serenity-Luxurious downtown condo!

3. Updated Vintage 1938 Log Cabin – Walk to Sister Bay

Updated Vintage 1938 Log Cabin – Walk to Sister Bay
Sister Bay
10.0 out of 10, Exceptional, (226 reviews)
"We had a great stay in Sister Bay! Perfect location within walking distance to all shops and restaurants. Would highly recommend staying here!"
United States
Cole M.
The price is NZ$977
includes taxes & fees
9 Nov - 10 Nov
Updated Vintage 1938 Log Cabin – Walk to Sister Bay

4. Private 3BR Gem on 2.5 Wooded Acres- Close to All

Private 3BR Gem on 2.5 Wooded Acres- Close to All
Sister Bay
10.0 out of 10, Exceptional, (61 reviews)
"Fantastic property - was perfect for our family of 5."
United States
Andrew L.
The price is NZ$890
includes taxes & fees
8 Nov - 9 Nov
Private 3BR Gem on 2.5 Wooded Acres- Close to All

5. Walk to Downtown! Wooded 4BR Sister Bay Home

Walk to Downtown! Wooded 4BR Sister Bay Home
Sister Bay
9.8 out of 10, Exceptional, (31 reviews)
"Nice clean property close to town."
United States
Nicole H.
The price is NZ$871
includes taxes & fees
15 Nov - 16 Nov
Walk to Downtown! Wooded 4BR Sister Bay Home

6. CONDO 5-Sister Bay Gem-Steps to the Beach

CONDO 5-Sister Bay Gem-Steps to the Beach
Sister Bay
10.0 out of 10, Exceptional, (22 reviews)
"Great location, exceptionally clean, prompt communication with contact person."
United States
Colleen K.
The price is NZ$736
includes taxes & fees
8 Nov - 9 Nov
CONDO 5-Sister Bay Gem-Steps to the Beach

7. CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.

CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.
Sister Bay
10.0 out of 10, Exceptional, (20 reviews)
"Excellent location! Condo was awesome with wonderful finishes. Very cozy and inviting. "
United States
Jason L.
The price is NZ$755
includes taxes & fees
30 Nov - 1 Dec
CONDO 4-Luxury Loft Retreat in Downtown Sister Bay.

8. Evergreen Hill Condominiums

Evergreen Hill Condominiums
3.5 star property
Fish Creek
9.4 out of 10, Exceptional, (82 reviews)
"Good location, good hotel. "
United States
shane
The price is NZ$278
includes taxes & fees
9 Nov - 10 Nov
Evergreen Hill Condominiums

9. Waterbury Inn

Waterbury Inn
2.5 star property
Ephraim
9.0 out of 10, Wonderful, (530 reviews)
"Great place to stay-beautiful location with great amenities"
United States
Megan
The price is NZ$424
includes taxes & fees
8 Nov - 9 Nov
Waterbury Inn

10. THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

THE CHARM of DOOR COUNTY - Cuteness and elegance combined!
Ephraim
9.8 out of 10, Exceptional, (98 reviews)
"Super cozy cottage just a short drive from town. Adorable courtyard with great landscaping. A perfect getaway for my mom and I to visit Door County!"
United States
Kayla V.
The price is NZ$505
includes taxes & fees
16 Nov - 17 Nov
THE CHARM of DOOR COUNTY - Cuteness and elegance combined!

11. Landmark Resort

Landmark Resort
3.5 star property
Egg Harbor
9.0 out of 10, Wonderful, (708 reviews)
"Beautiful property with spacious rooms and the staff helped me during my stay."
United States
Romaine
The price is NZ$347
includes taxes & fees
6 Dec - 7 Dec
Landmark Resort

12. Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi

Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi
Fish Creek
9.6 out of 10, Exceptional, (85 reviews)
"Great place, clean, great location!"
United States
Lynn M.
The price is NZ$280
includes taxes & fees
18 Nov - 19 Nov
Charming 2-bedroom cottage in Fish Creek with AC, heat, WiFi

13. Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay

Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (13 reviews)
"Smooth experience and easy communication with the host. Highly recommend!"
United States
Kristin G.
The price is NZ$1,067
includes taxes & fees
5 Dec - 6 Dec
Humbug Abode - located on beautiful 5 acres, minutes drive to Sister Bay

14. Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay

Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay
Ellison Bay
10.0 out of 10, Exceptional, (32 reviews)
"The house was clean and very comfortable! Everything we could have wanted was there- we discovered the drawer in the coffee table with games on night three:)Loved walking into Ellison Bay for dinner, sunsets and morning coffee.Will definitely stay here again!!"
United States
Molly C.
The price is NZ$1,144
includes taxes & fees
8 Nov - 9 Nov
Private Wooded Retreat w/ Hot Tub & Fireplace - Near Sister Bay

15. Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach
Ellison Bay
10.0 out of 10, Exceptional, (33 reviews)
"nice quiet house to stay in thats still close to all that Door County has to offer."
United States
Jamison M.
The price is NZ$1,148
includes taxes & fees
9 Nov - 10 Nov
Hot Tub, Family Friendly + 2 King Beds, Game Room, Secluded -Close to SB & Beach

16. Insta-worthy Waterfront Cottage with Hot Tub

Insta-worthy Waterfront Cottage with Hot Tub
Ellison Bay
10.0 out of 10, Exceptional, (46 reviews)
"Great house in a great location with friendly and very responsive hosts!"
United States
Bart T.
The price is NZ$1,435
includes taxes & fees
9 Nov - 10 Nov
Insta-worthy Waterfront Cottage with Hot Tub

17. Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape
Baileys Harbor
10.0 out of 10, Exceptional, (115 reviews)
"Amazing find! Beautiful place, well kept and has all the touches of home. The host was a great communicator and helpful! Definitely would recommend this place to a friend!"
United States
Crystal G.
The price is NZ$919
includes taxes & fees
9 Nov - 10 Nov
Red Cherry Woods Cottage 🍒 ~ Stylish Baileys Harbor Escape

18. Jacksonport Woodland Hearth Retreat - Near Lake Michigan

Jacksonport Woodland Hearth Retreat - Near Lake Michigan
Sturgeon Bay
10.0 out of 10, Exceptional, (8 reviews)
"Great place!"
United States
Anne W.
The price is NZ$757
includes taxes & fees
9 Nov - 10 Nov
Jacksonport Woodland Hearth Retreat - Near Lake Michigan

19. Sandy Toes Retreat,stunning view & just 25 steps to a sandy beach Lake Michigan.

Sandy Toes Retreat,stunning view & just 25 steps to a sandy beach Lake Michigan.
Cedar River
10.0 out of 10, Exceptional, (1 review)
"This was my first rental. we were amazed with the property. Cant wait to book again next year!"
United States
sally s.
The price is NZ$720
includes taxes & fees
8 Nov - 9 Nov
Sandy Toes Retreat,stunning view & just 25 steps to a sandy beach Lake Michigan.

20. Harbor View Penthouse Downtown Egg Harbor

Harbor View Penthouse Downtown Egg Harbor
Egg Harbor
10.0 out of 10, Exceptional, (4 reviews)
"All was wonderful! Beautiful property, perfect location."
United States
Beth D.
The price is NZ$1,360
includes taxes & fees
8 Nov - 9 Nov
Harbor View Penthouse Downtown Egg Harbor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sister Bay Hotel Reviews

Find out more about Sister Bay

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sister Bay holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sister Bay. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sister Bay. Seeing all the best attractions is bound to make you fall in love with Sister Bay. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sister Bay short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Sister Bay?

Yes, there are holiday rentals in Sister Bay close to Pirate's Cove Adventure Golf, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Sister Bay. Make sure you have time to check out the wineries and local tours during your trip.

What are some of the best holiday rentals that Sister Bay has to offer?

Great location! 5 BR 3 BA between Fish Creek and Ephraim, WI: This holiday home rental outside of Sister Bay offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Sister Bay?

With 89 Expedia holiday rentals, you're guaranteed to find just the right place for your Sister Bay stay.

What can I see and do in Sister Bay?

Lake Michigan and Waterfront Park are a couple of scenic spots to enjoy the outdoors, whereas Frykman Studio Gallery is one of the cultural attractions. While here, Sister Bay Beach and Sister Bay Marina are other places worth a visit.

What are holiday rentals like in Sister Bay?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sister Bay. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.