Vacation Rentals in Pleasantview Winery, MI: Compare 10+ Sites & Save

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310 Best Vacation Rentals in Pleasantview Winery (Starting from $147)

Southridge #9 - Ski-in/ski-out at base of Nub's Nob
Southridge #9 - Ski-in/ski-out at base of Nub's Nob
House
Harbor Springs, MI, USA
1.3k from Pleasantview Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Ski resorts

2 Bedrooms6 Guests
New to Booking
$470
Average price / night
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Secluded Log Cabin w/Sauna, Near Skiing & Golf
Secluded Log Cabin w/Sauna, Near Skiing & Golf
Cabin
Harbor Springs, MI, 49740, United States
0.2k from Pleasantview Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms12 Guests
10.0

Exceptional

12 reviews

$691
Average price / night
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Southridge 21
Southridge 21
Apartment
Harbor Springs, MI, USA
1.4k from Pleasantview Winery center

Apartments, Accommodations, Lodgings, Places to stay, Ski resorts

3 Bedrooms8 Guests
New to Booking
$429
Average price / night
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Happy Days and Nights -Sunset House- A 4 bedroom mansion close to skiing.
Happy Days and Nights -Sunset House- A 4 bedroom mansion close to skiing.
House
Harbor Springs, MI, 49740, United States
0.3k from Pleasantview Winery center

Arcade, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$740
Average price / night
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Southridge #2
Southridge #2
House
Harbor Springs, MI, USA
1.4k from Pleasantview Winery center

Cheap, Accommodations, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$354
Average price / night
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Mountain Cabin overlooking Boyne near Nubs W/ Hot Tub
Mountain Cabin overlooking Boyne near Nubs W/ Hot Tub
House
Harbor Springs, MI, 49740, United States
1.4k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms14 Guests
9.8

Exceptional

18 reviews

$717
Average price / night
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The Hidden Chalet
The Hidden Chalet
House
Harbor Springs, MI, USA
1.7k from Pleasantview Winery center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom12 Guests
New to Booking
$1203
Average price / night
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HARBOR SPRINGS 3 BEDROOM / 2 BATH COUNTRY CHALET
HARBOR SPRINGS 3 BEDROOM / 2 BATH COUNTRY CHALET
Ski Chalet
Harbor Springs, MI, 49740, United States
1.4k from Pleasantview Winery center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms10 Guests
9.8

Exceptional

53 reviews

$251
Average price / night
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Cozy 4BR Condo - Pool Access Near Ski & Lake
Cozy 4BR Condo - Pool Access Near Ski & Lake
House
Conway, MI, USA
2.1k from Pleasantview Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family, Condos

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$334
Average price / night
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Relax at the Cozy Cabin, just a 5-min drive to it all
Relax at the Cozy Cabin, just a 5-min drive to it all
House
Harbor Springs, MI, 49740, United States
1.4k from Pleasantview Winery center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$273
Average price / night
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Hideaway Valley Condo 36
Hideaway Valley Condo 36
Apartment
Pleasantview Winery, Harbor Springs, Michigan, USA
2.1k from Pleasantview Winery center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay, Family, Ski resorts, Condos

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$187
Average price / night
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Charming 3- BEDROOM/ 1 BATH Duplex Upper unit in Fabulous Harbor Springs.
Charming 3- BEDROOM/ 1 BATH Duplex Upper unit in Fabulous Harbor Springs.
House
Harbor Springs, MI, 49740, United States
1.6k from Pleasantview Winery center

AC, Barbecue, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, TV

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$189
Average price / night
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Heart & Soul Hideaway
Heart & Soul Hideaway
Apartment
Harbor Springs, MI, USA
2.1k from Pleasantview Winery center

Apartments, Accommodations, Pools, Lodgings, Vacation rentals, Places to stay, Ski resorts

4 Bedrooms7 Guests
New to Booking
$201
Average price / night
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Built for You - 4BR w/ Playground, Sauna, Games!
Built for You - 4BR w/ Playground, Sauna, Games!
House
Harbor Springs, MI, 49740, United States
1.7k from Pleasantview Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

4 Bedrooms13 Guests
10.0

Exceptional

9 reviews

$442
Average price / night
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Family Escape - Near Little Traverse Wheelway
Family Escape - Near Little Traverse Wheelway
House
Harbor Springs, MI, USA
2.6k from Pleasantview Winery center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$647
Average price / night
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Hemlock House in Harbor Springs Between Boyne Highlands & Nubs Nob
Hemlock House in Harbor Springs Between Boyne Highlands & Nubs Nob
House
Harbor Springs, MI, 49740, United States
1.7k from Pleasantview Winery center

Heater, Internet, No Smoking

1 Bedroom3 Guests
New to Booking
$187
Average price / night
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7 Mi to Dwtn - Family Condo in Harbor Springs!
7 Mi to Dwtn - Family Condo in Harbor Springs!
Apartment
Harbor Springs, MI, USA
2.9k from Pleasantview Winery center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$360
Average price / night
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Cozy Up-North Townhouse Bungalow
Cozy Up-North Townhouse Bungalow
House
harbor springs, MI, 49740, United States
1.7k from Pleasantview Winery center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

135 reviews

$147
Average price / night
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1 Mi to Nubs Nob Ski Resort Harbor Springs Condo
1 Mi to Nubs Nob Ski Resort Harbor Springs Condo
Apartment
Harbor Springs, MI, USA
2.9k from Pleasantview Winery center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Hot tubs, Places to stay, Condos

2 Bedrooms6 Guests
New to Booking
$409
Average price / night
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Cozy Chalet Getaway Near The Highlands - Sleeps 8
Cozy Chalet Getaway Near The Highlands - Sleeps 8
Ski Chalet
Harbor Springs, MI, 49740, United States
1.8k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$328
Average price / night
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Less Than 1 Mi to Nubs Nob Ski Cabin with Sauna and Deck!
Less Than 1 Mi to Nubs Nob Ski Cabin with Sauna and Deck!
House
Harbor Springs, MI, USA
2.9k from Pleasantview Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

5 Bedrooms18 Guests
New to Booking
$648
Average price / night
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Northern Michigan Getaway:Great Location for Outdoor Vacation!
Northern Michigan Getaway:Great Location for Outdoor Vacation!
Ski Chalet
Harbor Springs, MI, 49740, United States
1.8k from Pleasantview Winery center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
9.8

Exceptional

121 reviews

$244
Average price / night
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Newly renovated home in Harbor Springs is perfect for your ski, or beach getaway
Newly renovated home in Harbor Springs is perfect for your ski, or beach getaway
House
Harbor Springs, MI, 49740, United States
1.9k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

105 reviews

$291
Average price / night
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Beautiful Lower Level 3 Bedrooms Sleeps 8 Next to Nubs Nob and The Highlands
Beautiful Lower Level 3 Bedrooms Sleeps 8 Next to Nubs Nob and The Highlands
House
Harbor Springs, MI, 49740, United States
2.0k from Pleasantview Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.8

Exceptional

12 reviews

$341
Average price / night
Check Availability
“Year-Round Adventure Awaits – Ski, Golf & Relax in Harbor Springs!”
“Year-Round Adventure Awaits – Ski, Golf & Relax in Harbor Springs!”
House
Harbor Springs, MI, 49740, United States
2.0k from Pleasantview Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

122 reviews

$533
Average price / night
Check Availability
Northern Enclosure Lodge - Four Season Retreat
Northern Enclosure Lodge - Four Season Retreat
Ski Chalet
Harbor Springs, MI, 49740, United States
2.0k from Pleasantview Winery center

Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

146 reviews

$291
Average price / night
Check Availability
Location, Location, Location !!
Location, Location, Location !!
House
Harbor Springs, MI, 49740, United States
2.0k from Pleasantview Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
9.4

Superb

13 reviews

$362
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Pleasantview Winery.

Pleasantview Winery Vacation Rentals on the Map

Frequently Asked Questions

You can explore 310 verified vacation rentals in Pleasantview Winery. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Pleasantview Winery vary depending on the season, property size, and location. Rates typically start from around $147 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Pleasantview Winery include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Pleasantview Winery welcome pets. Currently, 18 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Pleasantview Winery often include amenities such as Fireplace/Heating, Wellness Facilities, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.