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Lakeside Vacation Rentals near Wineries

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    Don't let other travelers get your favorite Lakeside area vacation rental. You're so close to securing your perfect getaway. Book today.
    25 Matching Rentals in the Lakeside AreaView all 55 rentals
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    Classic 5BR Lk MI Cottage a Short Walk To the Beach1 / 22
    (6)Excellent
    Lakeside
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Nearby are Warren Dunes, kayaking on the Galien River, wineries/breweries, and great restaurants, but we had the most fun just hanging right around the cottage.
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    Lakeside
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 5 miles of Lakeside.
    Blue Skies and Beach Dreams1 / 14
    (3)Excellent
    New Buffalo
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Charming, Updated Sawyer Dune Cottage--Next to Warren Dunes + Private Beach!1 / 21
    (3)Excellent
    Sawyer
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • DVD Player
    • Washer
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 2017
    Super enjoyed our weekend with 3 kids in this cottage. Attentive owners with updated eclectic decor. Spent most of our time in their screened in porch playing games and enjoying...
    Reviewed July 12, 2017
    My husband and I and our three kids loved this house! It was very clean and had everything we needed, plenty of room, very well stocked and an amazing front porch! The beach was...
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    About this property
    You found it--the perfect location near everything Harbor County has to offer in the beautiful, wooded and private Shorewood Hills beach community. This charming 1940s dune cottage near Sawyer, MI is the best of both worlds, situated next to Warren Dunes State Park but with all the amenities of a...
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    Location Information
    Sawyer, Berrien County 49125
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Harbert
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Haven is a peaceful spacious home with 4 bedrooms, 2 baths, 2 fireplaces, 2 decks, front porch, outdoor fire pit, & BBQ . The 11 acres provide for exploring the woods and privacy. The decks are for enjoying outdoor living, this is the perfect place to enjoy Harbor Country lifestyle. Located...
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    Harbert, Berrien County 49128
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lemonade Cottage-Spring Getaway - walk to town, private backyard with hot tub!1 / 31
    (4)Excellent
    New Buffalo
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2017
    What a fantastic cottage! My friend and I used the hot tub, so relaxing! Everything was perfect! Can't wait until next year!
    Reviewed August 7, 2017
    This was our 2nd time staying here. We love it! Everything is kept up well and clean. The hot tub and fit pit are a great add on that we enjoy.
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    About this property
    This thoughtfully decorated, cozy cottage is the perfect setting for a ladies' weekend or small family vacation. It has a updated kitchen and bath, two bedrooms (one queen bed and two twin beds), as well as a sleeper sofa and additional couch. The living room has a large flat screen TV with...
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    New Buffalo, Berrien County 49117
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Amish log cabin located by Warren Dunes State Park and Greenbush brewery1 / 6
    (3)Very good
    Sawyer
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Parking
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2017
    The Red Arrow Cabins are as cute as can be. After an afternoon of winery hopping in Baroda to celebrate a friends birthday, myself and 4 other friends spent the night at the...
    Reviewed September 14, 2017
    My daughter and I stayed in Red Arrow Cabins at the Driftwood cabin in late August. Our cabin had 1 bedroom and loft. The cabin was so cute and cozy and the beds were very...
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    About this property
    This warm inviting cabin features, wood burning stove, heat/ac, covered front porch, fire pit, grill, outdoor picnic table, kitchenette and bathroom with a hot shower. Conveniently located near State Park, restaurants, breweries, wineries, golf courses and shopping. Great place to relax and unwind....
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    Location Information
    Sawyer, Berrien County 49125
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Three Oaks
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lily's Cottage in Three Oaks, MI is steps away from the from the Journeyman Distillery / Staymaker, Acorn Theater, and the Featherbone Factory along with the boutiques and shops on main street. The farms, wineries, and beaches of Lake Michigan are a short drive. Lily’s Cottage is a...
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    Three Oaks, Berrien County 49128
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Large Lake Michigan Home at Warren Dunes sleeps 241 / 48
    (13)Excellent
    Sawyer
    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Porch
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 13, 2016
    We stayed with a large group of friends, adults and kids, over the weekend. The house was perfect even with a large group due to the two seating areas. The kitchen was well...
    Reviewed December 31, 2015
    We had 19 of us stay here with plenty of room to gather together and yet have space to retreat when necessary. The beach is less than a mile walk and the dunes are even closer...
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    About this property
    Our vacation home known as Dunehaven is a year-round retreat amidst towering pines just steps from the world's largest freshwater dunes located in Warren Dunes State Park, Sawyer, Michigan. Walk out the backyard right into the park and an adventure awaits! This spacious home with over 5,400...
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    Sawyer, Berrien County 49125
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    Union Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 21, 2014
    The air was fresh, the beach was relaxing and the house was accommodating. The kitchen is fully stocked. Could not ask for more. Easy check in and Check out.
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    About this property
    Lovely home, perfect for a family vacation!!! It is NEWLY REDONE!!! NEW FURNITURE!!!! NEW BEDS !! NEW WALLS, NEW BATHROOM, NEW FLOORS IN MAIN AREA. VERY CLEAN!!! NEW HOUSE KEEPER. Decorated comfortably and has 3 bedrooms and a Family room that can sleep 2 people. The bedrooms have 2 full beds and...
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    Location Information
    Union Pier, Berrien County 49129
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Eco-LuxeYear-Round Secluded Lakefront House-Hotub,2 Fireplcs-90 min from Chicago1 / 184
    (17)Excellent
    Union Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great hikes are nearby up the Dunes, wineries, or to fabulous beaches and coves.
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Housekeeping Included
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 25, 2017
    All I have to say is this house is amazing, super clean, meticulously cared for, beautiful design layout with stunning architectural details on the lake! It will take me more...
    Reviewed November 13, 2016
    My husband, toddler and I stayed here for ten days to celebrate our anniversary and daughter's third birthday and we truly enjoyed Sanctuaire. Gorgeous views of the lake and...
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    About this property
    SECLUDED & PRIVATE LAKEFRONT Retreat. Award winning and Located 90 minutes from Chicago in the Heart of the Wine Country in SouthWest Michigan. ALL THE BELLS AND WHISTLES! • 2000 Square Feet * LAKEFRONT with 200 feet of private lakefront footage • New 25K Hot Tub- open year round and...
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    Location Information
    Union Pier, Berrien County 49101
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Buffalo
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Private Yard
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Barton Street Bungalow! Our home is located in the heart of New Buffalo, Michigan, where you can experience the relaxing charm of this quintessential Michigan beach town while you enjoy deluxe, resort quality accommodations in this beautifully furnished, classic arts and crafts home...
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    Location Information
    New Buffalo, Berrien County 49117
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sawyer
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boasting 3 miles of Lake Michigan Shoreline, 6 miles of hiking trails and spectacular views all around, Warren Dunes State Park is the perfect year-round playground. Bring your family and 4-legged friends along for a memorable stay 1 mile from the park at this 3-bedroom, 1.5-bath Sawyer house for...
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    Location Information
    Sawyer, Berrien County 49125
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Harbert
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in this charming family cottage in Harbert with 3 spacious bedrooms and 1 full bathroom in the main house and 1 full bathroom and well-equipped kitchenette in the separate studio apartment. With 2 dwellings, this home offers privacy and enough space for up to 12 guests. The interiors of both...
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    Location Information
    Harbert, Berrien County 49128
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Union Pier
    10 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    • Washer
    • Patio
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please see our goldberrywoods site for more details. Prime Summer dates available! We currently have the Labor Day weekend available for groups (sleeps 16-24 people). Add 1 or 2 cottages to accommodate 10-20 more! Come and stay in the heart of Harbor Country on 28 secluded acres of woods with...
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    Location Information
    Union Pier, Berrien County 49129
    Rental Home - 10 Bedrooms, 9 Bathrooms, Sleeps 24
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    Union Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ALEX COTTAGE SLEEPS: 4 BEDROOMS: 2 BATHROOMS: 1 PARKING SPOT: 1 *STEPS FROM LAKEFRONT SORRY, NO PETS ALLOWED *PLAYGROUND ON-SITE *3 other cabins surround Alex that are available for rent. (NO Pets are allowed at any of our Union Pier Cottages) Alex Cabin is located steps away from your private...
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    Location Information
    Union Pier, Berrien County 49129
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Union Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Private Indoor Pool
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Sauna
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape from the city life to 'Asolare,' the luxurious 4-bedroom, 4-bathroom Union Pier vacation rental house located just 2 blocks from the serene Michigan coastline. This 3,500-square-foot property fits up to 16 lucky guests and has a multitude of different amenities to make for a trip you will...
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    Location Information
    Union Pier, Berrien County 49129
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    Union Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated cottage. A beautiful 2 bedroom 1 bath cottage 2 blocks from beach. Perfect for a family vacation!!! It is decorated comfortably and has 2 bedrooms and can sleep 4 people. The bedrooms have queen beds. Best of all, this home is located less than 1 mile from the beach. It is also...
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    Location Information
    Union Pier, Berrien County 49129
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Union Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GRACE COTTAGE SLEEPS: 6 BEDROOMS: 3 BATHROOMS: 2 PARKING SPOTS AVAILABLE: 2 MAX SORRY, NO PETS ALLOWED *STEPS FROM LAKEFRONT (Lake Michigan) *3 Cabins surround Grace that are available for rent. (Pets are NOT allowed at any of our Union Pier Cottages) Stay steps away from the Michigan lakefront,...
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    Location Information
    Union Pier, Berrien County 49129
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Union Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    HARBOR HAVEN SLEEPS: 4 BEDROOMS: 2 BATHROOMS: 1.5 *NEIGHBORHOOD VIEW…LAKE MICHIGAN BEACH BLOCKS AWAY Perfect home for a family of 4 looking for a simple, clean, vacation spot. Harbor Haven is just a short 8 minute walk or 3 minute drive to a gorgeous beach on Lake Michigan! The home comes with...
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    Location Information
    Union Pier, Berrien County 49129
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    NEW! 2BR Sawyer Apt - 5 mins to Warren Dunes Park!1 / 24
    (1)Average
    Sawyer
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Pros: convenient location, easy to book & pay, clean, updated kitchen & bath, site manager was fairly responsive. Cons: email confirmation check in was earlier than the...
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    About this property
    *Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay* Escape to Sawyer and stay at this 2-bed, 1-bath vacation rental apartment that sleeps 4! Located in the heart of the city, this apartment will give you the luxuries...
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    Sawyer, Berrien County 49125
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sawyer
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best of Sawyer while staying at this 1-bath vacation rental studio cabin that sleeps 2 adults and up to 3 children with a small additional fee over 4. You'll have a private fenced-in outdoor space, a driveway with separate parking and if you're traveling with a larger group there is...
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    Location Information
    Sawyer, Berrien County 49125
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Union Pier
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the pristine beaches and beautiful countryside of Union Pier from this 4-bedroom, 2-bathroom vacation rental house. Boasting over 1,000 square feet of living space, this home offers sleeping accommodations for up to 14, a spacious backyard area with a hot tub, and an unrivaled location....
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    Union Pier, Berrien County 49129
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 14
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    Three Oaks
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Southwestern Michigan by staying at this delightfully quaint Three Oaks vacation rental home! Featuring 2 bedrooms, 1 bathroom, a beautiful fenced-in yard and close location to a variety of area attractions, this cozy house is perfect for your next Michigan getaway. THE...
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    Three Oaks, Berrien County 49644
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sawyer
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your next trip to Sawyer an unforgettable one by staying at this charming 2-bedroom, 1-bedroom vacation rental condo sleeping 7. Situated in a duplex, this private escape offers several modern amenities, a fire pit, and a prime location just 5 minutes from Warren Dunes State Park. Whether you...
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    Location Information
    Sawyer, Berrien County 49125
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    68° 48°
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    October
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