Holiday Homes in Cheboygan

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Featured Holiday Homes in Cheboygan

Cozy Up-North Townhouse Bungalow

9.6 out of 10, Exceptional, (97)
"I enjoy staying here, this was a repeat visit. Great landlord, condo is so well stocked and homey and clean."
Cozy Up-North Townhouse Bungalow

Walk To The Lake, Beach, Indoor Waterpark And Downtown

6.4 out of 10, (74)
"The house was secluded so that was a huge plus. Plenty of parking as well if you have multiple cars. Communication with host was lacking until the week of the stay. That aside, very nice stay."
Walk To The Lake, Beach, Indoor Waterpark And Downtown

Victorian charmer just steps from the lake!

9.6 out of 10, Exceptional, (19)
"This is a beautiful place to stay while in St. Igance. Very clean, decor is beautiful, spacious home and gracious host. Highly recommend!"
Victorian charmer just steps from the lake!

New Listing! Close to Petoskey & Crooked Lake boat launch. A Gem!

10.0 out of 10, Exceptional, (32)
"Absolutely Perfect Getaway! We had an incredible experience at this property! From the moment we arrived, everything was spotless and beautifully maintained. The home was even better than the photos—cozy, and thoughtfully decorated. The location was ideal—close to local attractions yet peaceful and private. This was truly one of the best stays we’ve ever had, and we can’t wait to come back! Highly recommend this property for anyone looking for a relaxing getaway. "
New Listing! Close to Petoskey & Crooked Lake boat launch. A Gem!

Up North Vacations Home in the Heart of Indian River "Exit 310"

9.8 out of 10, Exceptional, (69)
"The property was great, very clean and a smooth stay overall! "
Up North Vacations Home in the Heart of Indian River "Exit 310"

Unique Petoskey House-Walking Distance to Downtown

8.6 out of 10, Excellent, (43)
"Cute place inside, lots of room for a family and close all the things we wanted to do so it was great! "
Unique Petoskey House-Walking Distance to Downtown

The Highlands - Brand New Beautiful Addition - 7 Bedrooms, Ski-In/Ski-Out!

10.0 out of 10, Exceptional, (83)
"This was an excellent property for our group. We enjoyed the space and all the amenities such as the hot tub, the outdoor grill and fire pit and the numerous bedrooms and bathrooms. The kitchen was well stocked for cooking and the house was extra clean. Our group consisted of eight men vying for our annual golf championship. A wouderful time was had by all."
The Highlands - Brand New Beautiful Addition - 7 Bedrooms, Ski-In/Ski-Out!

Downtown Harbor House

8.4 out of 10, Very good, (26)
"Classic Michigan cottage with all the charm. Great location."
Downtown Harbor House

Trout Creek Resort/Fall Colors/Skiing/Pool/Hot tub/Sauna/Pet friendly

10.0 out of 10, Exceptional, (24)
"The whole process with the condo was easy. The hosts were very responsive to questions and concerns. The condo was clean and inviting. Will definitely be staying again."
Trout Creek Resort/Fall Colors/Skiing/Pool/Hot tub/Sauna/Pet friendly

Makwa North in St Ignace – God’s Country by Mackinac Island

9.6 out of 10, Exceptional, (19)
"Very clean and easy to find. Located close to shops and resturants."
Makwa North in St Ignace – God’s Country by Mackinac Island

Pet-Friendly Harbor Springs Home Near Ski Resorts!

8.6 out of 10, Excellent, (20)
"Beautiful Home and surrounding. Lacks in furnishings if more than 4 people. Kitchen needs attention "
Pet-Friendly Harbor Springs Home Near Ski Resorts!

Cozy Chic of Cheboygan: Private Main Level - Hot Tub, Tanning & Massage Chair!

10.0 out of 10, Exceptional, (16)
"We had a very nice and cozy stay with our little family and dog. The little touches and super clean house make you feel right at home. The only downside is you do hear the family upstairs sometimes (that is disclosed in the description) so it feels a little less private. Still it’s a very nice stay and we had a great time. "
The price is AU$459
includes taxes & fees
11 Dec - 12 Dec
Cozy Chic of Cheboygan: Private Main Level - Hot Tub, Tanning & Massage Chair!

Relaxing Lake View Home, Pet Friendly, Central Location. Close to Ferries!

10.0 out of 10, Exceptional, (13)
"Nice large home. Extremely clean! I always take my own cleaning things and didn’t need to clean a thing. Loved TV’s in all bedrooms. Perfect location to see all this area has. Hosts respond very fast. Beautiful view of the water…..:)"
Relaxing Lake View Home, Pet Friendly, Central Location. Close to Ferries!

Family and Friends 4 Bedroom Newer Vacation Home

9.2 out of 10, Wonderful, (40)
"The polished Petoskey stones that Al left for us were beautiful. The house was clean & the beds were comfortable. "
Family and Friends 4 Bedroom Newer Vacation Home

Cheboygan’s Bellant Street Bungalow - Northern Michigan Destination Hotspot!

9.2 out of 10, Wonderful, (31)
"Good location with easy access to Mackinaw City and the UP. Although we could not locate the fourth bedroom."
The price is AU$317
includes taxes & fees
3 Dec - 4 Dec
Cheboygan’s Bellant Street Bungalow - Northern Michigan Destination Hotspot!

Perfect in-town Petoskey licensed full house rental new kitchen. Always clean.

9.8 out of 10, Exceptional, (114)
"Great stay, as always!"
Perfect in-town Petoskey licensed full house rental new kitchen. Always clean.

Your vacation starts here! Fully Furnished 3 bedroom home! Close to Ferry's!

9.8 out of 10, Exceptional, (75)
"Never a bad stay. No such thing.Property is clean, secure, is as described and close to everything you might need. Would recommend to all and will stay again if the propery owner will have us!"
Your vacation starts here! Fully Furnished 3 bedroom home! Close to Ferry's!

Cozy 4-bedroom house in Harbor Springs! 5 minutes to Nub's Nob & Boyne Highlands

10.0 out of 10, Exceptional, (5)
"Great location and accommodations. The house had everything we needed for a great long weekend guys trip. Communication with the owner was professional and quick. Very clean house! Overall a great vacation."
Cozy 4-bedroom house in Harbor Springs! 5 minutes to Nub's Nob & Boyne Highlands

Black Lake sunset waterfront home 78' private sandy beach on prestine Black Lake

10.0 out of 10, Exceptional, (35)
"This house was wonderful to stay in. The beach was great, a little dirty but my 2 and 1 year olds loved it. The house was as advertised. A lot of spiders but that is to be expected with a lake house. The kitchen was well stocked. The beds were pretty uncomfortable but not unbearable. The neighbors are the hosts of the home and were very inviting. "
Black Lake sunset waterfront home 78' private sandy beach on prestine Black Lake

T&J Cozy Cottage on Crooked River - Enjoy a family or romantic getaway

10.0 out of 10, Exceptional, (76)
"Great communication by hosts, check in and out was a breeze. In a great central location between Indian River, Petoskey/Harbor Springs, and Mackinaw City. Arrived to a clean, well stocked home. In the kitchen, lots of pans and plates. Seasoning cabinet well stocked, with some coffee and kuerig pods. Lots of mugs including an ugly one with a block M on it. Bathroom was clean, shower with good water pressure. Only used the master bedroom, but the bed was comfortable and there was plenty of...
T&J Cozy Cottage on Crooked River - Enjoy a family or romantic getaway
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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Other property types in Cheboygan

Cozy Chic of Cheboygan: Private Main Level - Hot Tub, Tanning & Massage Chair!

10.0 out of 10, Exceptional, (16)
"We had a very nice and cozy stay with our little family and dog. The little touches and super clean house make you feel right at home. The only downside is you do hear the family upstairs sometimes (that is disclosed in the description) so it feels a little less private. Still it’s a very nice stay and we had a great time. "
The price is AU$459
includes taxes & fees
11 Dec - 12 Dec
Cozy Chic of Cheboygan: Private Main Level - Hot Tub, Tanning & Massage Chair!

Wifi, lakefront, bike trail access. Ask about 2 free ferry tickets!!

9.8 out of 10, Exceptional, (56)
"The location on Lake Huron was gorgeous, and the hosts were lovely!"
Wifi, lakefront, bike trail access. Ask about 2 free ferry tickets!!

Family cottage on Lake Huron, 4 bedrooms/2 bathrooms. Sleeps 7, Pet-friendly!

9.8 out of 10, Exceptional, (18)
"Awesome place"
Family cottage on Lake Huron, 4 bedrooms/2 bathrooms. Sleeps 7, Pet-friendly!
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.