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

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39 Best Cottage Rentals in Pleasantview Winery (Starting from $160)

Harbor Springs 2 Bedroom Cottage Close to Boyne Highlands & Nubs Nob
Harbor Springs 2 Bedroom Cottage Close to Boyne Highlands & Nubs Nob
Cottage
Harbor Springs, MI, 49740, United States
2.4k from Pleasantview Winery center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms8 Guests
9.8

Exceptional

256 reviews

$175
Average price / night
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Charming garden cottage on the bike path with Scenic backyard in Harbor Springs
Charming garden cottage on the bike path with Scenic backyard in Harbor Springs
Cottage
Harbor Springs, MI, 49740, United States
2.7k from Pleasantview Winery center

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

2 Bedrooms4 Guests
9.2

Superb

5 reviews

$304
Average price / night
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Charming 5-bedroom Roaring Brook cottage in Harbor Springs with beach access.
Charming 5-bedroom Roaring Brook cottage in Harbor Springs with beach access.
Cottage
Harbor Springs, MI, 49740, United States
3.6k from Pleasantview Winery center

Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Tennis Court

5 Bedrooms10 Guests
9.0

Fabulous

2 reviews

$576
Average price / night
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 Harbor Springs 4-bedroom cottage.
Harbor Springs 4-bedroom cottage.
Cottage
Harbor Springs, MI, 49740, United States
3.6k from Pleasantview Winery center

Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, TV

4 Bedrooms10 Guests
8.8

Fabulous

3 reviews

$705
Average price / night
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Birchgate – Historic Bluffside Cottage with Panoramic Bay Views
Birchgate – Historic Bluffside Cottage with Panoramic Bay Views
Cottage
Harbor Springs, MI, 49740, United States
3.7k from Pleasantview Winery center

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

5 Bedrooms14 Guests
10.0

Exceptional

2 reviews

$672
Average price / night
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Rustic 5-bedroom cottage with private beach near Harbor Springs
Rustic 5-bedroom cottage with private beach near Harbor Springs
Cottage
Harbor Springs, MI, 49740, United States
4.0k from Pleasantview Winery center

Dryer, Heater, Internet, Laundry, No Smoking, Toys, Washer

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$718
Average price / night
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Park Walk Place - Lovely 4 bd / 2 bth cottage, newly decorated w/ renovations
Park Walk Place - Lovely 4 bd / 2 bth cottage, newly decorated w/ renovations
Cottage
Harbor Springs, MI, 49740, United States
4.8k from Pleasantview Winery center

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

4 Bedrooms8 Guests
New to Booking
$1104
Average price / night
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Weque! Close to Nub's Nob and Boyne Highlands!
Weque! Close to Nub's Nob and Boyne Highlands!
Cottage
Harbor Springs, MI, 49740, United States
5.0k from Pleasantview Winery center

Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms11 Guests
9.6

Exceptional

5 reviews

$1279
Average price / night
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Pine Corner Cottage - recently renovated in heart of Harbor Springs
Pine Corner Cottage - recently renovated in heart of Harbor Springs
Cottage
Harbor Springs, MI, 49740, United States
5.2k from Pleasantview Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

34 reviews

$545
Average price / night
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FAMILY FRIENDLY COTTAGE SLEEPS 12 !!! BEAUTIFULLY UPDATED
FAMILY FRIENDLY COTTAGE SLEEPS 12 !!! BEAUTIFULLY UPDATED
Cottage
Petoskey, MI, 49770, United States
5.8k from Pleasantview Winery center

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

4 Bedrooms12 Guests
9.6

Exceptional

87 reviews

$272
Average price / night
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Wonderful Downtown Harbor Springs Cottage, quick walk to shops and restaurants!
Wonderful Downtown Harbor Springs Cottage, quick walk to shops and restaurants!
Cottage
Harbor Springs, MI, 49740, United States
5.9k from Pleasantview Winery center

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

3 Bedrooms6 Guests
10.0

Exceptional

57 reviews

$507
Average price / night
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Amazing Carriage House & Yard w/Private (heated) GARAGE in the HEART of TOWN!
Amazing Carriage House & Yard w/Private (heated) GARAGE in the HEART of TOWN!
Cottage
Harbor Springs, MI, 49740, United States
6.0k from Pleasantview Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

104 reviews

$446
Average price / night
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Kay's Haven on Crooked Lake
Kay's Haven on Crooked Lake
Cottage
Petoskey, MI, 49770, United States
6.3k from Pleasantview Winery center

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

3 Bedrooms8 Guests
9.6

Exceptional

10 reviews

$535
Average price / night
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Charming 4-bedroom cottage in adorable Oden with WiFi, AC
Charming 4-bedroom cottage in adorable Oden with WiFi, AC
Cottage
Alanson, MI, 49706, United States
6.5k from Pleasantview Winery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
9.4

Superb

3 reviews

$375
Average price / night
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Ann Street Cottage. 10 minute drive to skiing, 10 minute walk to downtown
Ann Street Cottage. 10 minute drive to skiing, 10 minute walk to downtown
Cottage
Harbor Springs, MI, 49740, United States
6.6k from Pleasantview Winery center

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

2 Bedrooms4 Guests
9.8

Exceptional

30 reviews

$250
Average price / night
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Harbor Springs Cottage In The Woods
Harbor Springs Cottage In The Woods
Cottage
Harbor Springs, MI, 49740, United States
6.6k from Pleasantview Winery center

AC, Barbecue, Dryer, Free Parking, Heater, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

107 reviews

$229
Average price / night
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Harbor Shady Acre Cottage Next to Nature Preserve and Minutes From Downtown HS
Harbor Shady Acre Cottage Next to Nature Preserve and Minutes From Downtown HS
Cottage
Harbor Springs, MI, 49740, United States
6.8k from Pleasantview Winery center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
7.0

Good

2 reviews

$775
Average price / night
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Luxury Lake Home with Private Dock 
Luxury Lake Home with Private Dock 
Cottage
Petoskey, MI, 49770, United States
6.9k from Pleasantview Winery center

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

5 Bedrooms14 Guests
10.0

Exceptional

19 reviews

$1022
Average price / night
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Little Bay Breeze: Charming Vacation Cottage in Petoskey
Little Bay Breeze: Charming Vacation Cottage in Petoskey
Cottage
Petoskey, MI, 49770, United States
7.1k from Pleasantview Winery center

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

2 Bedrooms4 Guests
9.4

Superb

11 reviews

$258
Average price / night
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Waterfront Alanson Cottage w/ Dock & Lake Access!
Waterfront Alanson Cottage w/ Dock & Lake Access!
Cottage
Alanson, MI, 49706, United States
7.4k from Pleasantview Winery center

Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

5 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$422
Average price / night
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Historic 5BR Cottage Near Trails with Crooked Lake Views
Historic 5BR Cottage Near Trails with Crooked Lake Views
Cottage
Alanson, MI, 49706, United States
7.8k from Pleasantview Winery center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
9.4

Superb

69 reviews

$413
Average price / night
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Charming cottage on Crooked Lake - the ideal retreat for families & friends!
Charming cottage on Crooked Lake - the ideal retreat for families & friends!
Cottage
Alanson, MI, 49706, United States
7.9k from Pleasantview Winery center

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

4 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$459
Average price / night
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Crooked Lake Cottage with sandy swimming beach
Crooked Lake Cottage with sandy swimming beach
Cottage
Alanson, MI, 49706, United States
7.9k from Pleasantview Winery center

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

2 Bedrooms6 Guests
9.8

Exceptional

51 reviews

$359
Average price / night
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Cottage Home Crooked Lake Alanson by Petoskey Harbor Springs Mackinac WIFI Cable
Cottage Home Crooked Lake Alanson by Petoskey Harbor Springs Mackinac WIFI Cable
Cottage
Oden, MI, 49764, United States
8.2k from Pleasantview Winery center

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

2 Bedrooms6 Guests
9.6

Exceptional

67 reviews

$173
Average price / night
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'Tiny House Cottage 5' w/ Crooked Lake Access!
'Tiny House Cottage 5' w/ Crooked Lake Access!
Cottage
Alanson, MI, 49706, United States
8.2k from Pleasantview Winery center

AC, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

13 reviews

$160
Average price / night
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Stay On The Tunnel Of Trees Scenic Highway
Stay On The Tunnel Of Trees Scenic Highway
Cottage
Harbor Springs, MI, 49740, United States
8.9k from Pleasantview Winery center

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

2 Bedrooms8 Guests
10.0

Exceptional

18 reviews

$375
Average price / night
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2 Bedroom-4 Bed Cottage Near Local Ski Resorts! Stay at True North Golf Club
2 Bedroom-4 Bed Cottage Near Local Ski Resorts! Stay at True North Golf Club
Cottage
Harbor Springs, MI, 49740, United States
9.0k from Pleasantview Winery center

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

2 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$815
Average price / night
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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 Cottage Rentals in Pleasantview Winery.

Pleasantview Winery Cottage Rentals on the Map

Frequently Asked Questions

You can explore 39 verified cottage rentals in Pleasantview Winery. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Pleasantview Winery vary based on the season, location, and amenities offered. Rates typically start from around $160 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Pleasantview Winery feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 11 listings in Pleasantview Winery welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Pleasantview Winery are known for their comfort and charm, often including amenities such as Bedding/Linens, Wellness Facilities, and Fireplace/Heating. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Pleasantview Winery are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.