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Pet Friendly Holiday Rentals in Lakeside

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    Don't let other travellers get your favourite Lakeside area holiday rental. You're so close to securing your perfect getaway. Book today.
    16 Matching Rentals in the Lakeside AreaView all 58 rentals
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    2 FUN 4 Bedroom 2 Bath COTTAGES each Sleep 10 people Beach-Pool-Hot Tub and More1 / 21
    (20)Very good
    Lakeside
    8 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Lakeside
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lakeside
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 10 kilometres of Lakeside.
    Eco-Secluded Lakefront House-Hot Tub-90 min from Chicago-Featured in NY Times!1 / 188
    (17)Excellent
    Union Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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 25 February 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 13 November 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 in Baroda. • 2000 Square Feet * LAKEFRONT with 200 feet of private lakefront footage • New 25K Hot Tub- open year round and professionally serviced 3x...
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    Location Information
    49101, Union Pier, Berrien County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Everything Is New From Beds To Kitchen Cabinets1 / 24
    (3)Excellent
    New Buffalo
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2017
    My girlfriends and I spent 2 nights at Ed and Deb's cottage. It was spotless and cozy. Everything we needed was there. Ed was a very nice, friendly man who gave us plenty of...
    Reviewed 11 August 2017
    This home is VERY clean and has everything you need for a great vacation - fenced in yard, bonfire pit with firewood, grill (which was extremely clean... much cleaner than mine...
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    About this property
    Fresh 2 Bedroom Home That Sleeps 6 With Hide-a-bed. Located central to everything 1/4 mile from Lake Michigan, 5 minutes from Four Winds Casino, Blue Chip Casino and two golf courses and the Lighthouse place outlet mall. Rental supplied with 2 passenger golf cart but you can upgrade to 4...
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    Location Information
    49117, New Buffalo, Berrien County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    5* rated. Block to Lake MI. Golf Cart (seasonal). Secluded.1 / 28
    (6)Excellent
    New Buffalo
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2019
    We love Treetops and have made it our summer family tradition to spend a week there together. The home is very comfortable and has all the amenities of home plus more. No need...
    Reviewed 22 August 2019
    We can not say enough about this amazing property and owner, We've been there twice, and have already booked our return trip for next summer.The house is beautiful and...
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    About this property
    Very private home on a sand dune set away from neighbors. Aptly decorated for your beach vacation. Block to Lake Michigan. Golf cart included (in season). As we run on multiple sites please know that we have 100+, 5-star reviews in total (and only 5 star) in four seasons of owning/renting the...
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    Location Information
    49117, New Buffalo, Berrien County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Union Pier
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete renovation inside and out of a split level 4 bed (3 king size and 1 bedroom w 2 twins) 2 bath with fireplace on very private 23 acres. Renovation was just completed Mid century modern and industrial decor. Hardwood floors through out downstairs, new carpet upstairs, Huge fire pit, screened...
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    Location Information
    49129, Union Pier, Berrien County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    ‘Asolare’ Union Pier House w/Pool/Game Room/Tennis1 / 28
    (1)Excellent
    Union Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • 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
    Reviewed 26 August 2018
    We thoroughly enjoyed this home with 7 adults, one toddler and one dog. The beds are comfortable, the kitchen is very well furnished and the grill is great. There are lots of...
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    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
    49129, Union Pier, Berrien County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
    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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    Location Information
    49128, Harbert, Berrien County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    New Buffalo
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • DVD Player
    • Balcony
    • Housekeeping Included
    • Central Heating
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our beautiful new home! Lots of love went into building and designing our 2nd home. We love to host large gatherings of family and friends and this home does not disappoint. A top Chicago designer was involved every step of the way from layout to furnishings ~ it will feel like you...
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    Location Information
    49117, New Buffalo, Berrien County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Union Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Parking
    • Private Garden
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Country Cottage is fully furnished located on a 1/4 acre lot with parking available for up to 5 vehicles. Our spacious accommodations will provide you with: 7 Wonderful rooms. 3 Bedrooms - (bed linens provided) 2 Full Baths (Bath towels provided) Fully equipped kitchen with dishwasher,...
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    Location Information
    49129, Union Pier, Berrien County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Walking Distance to New Buffalo Beach, Marina1 / 21
    (6)Average
    New Buffalo
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Patio
    • Parking
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2019
    My friend, her two grandchildren, my own daughter & I stayed here August 5-8 and was disappointed in the location. It is not within an easy walking distance of beach and it...
    Reviewed 1 September 2017
    We really enjoyed our stay at Auggie’s. The owner was a pleasure to work with – promptly replied to emails and was very accommodating to our needs. The house is well suited for...
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    About this property
    Cape Cod Surf House has beautiful cathedral ceilings with plenty of sky lights. Upstairs Master bedroom has full size bed, breakfast table, and large window overlooking private woods. Also upstairs is a open loft area with another bedroom with a full size bed and many popular novels. Perfect to...
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    Location Information
    49117, New Buffalo, Berrien County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    New Buffalo
    5 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    24 square feet, sleeps 16 walking distance to beach/downtown & a large yard This wine themed home, owned by the same owners as Proměny Olive & Wine, has 2400 square feet and is located in a quiet lakefront town, known as the Hamptons of Chicago. New Buffalo is a popular summer getaway for those...
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    Location Information
    49117, New Buffalo, Berrien County
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 16
    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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    Location Information
    49129, Union Pier, Berrien County
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 14
    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
    49125, Sawyer, Berrien County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Sawyer
    3 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make ‘Peacock Place’ your new go-to Sawyer destination! Whether you’re in town for a getaway with the girls or a family reunion, this is an ideal rental for you! This 3-bedroom + Den, 2.5-bath vacation rental house sleeps 12 with flexibility for up to 16 and features a private driveway + parking,...
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    Location Information
    49125, Sawyer, Berrien County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 16
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