Home Vacation Rentals By Owner In Lakeside, MI

Showing 60 Of 65 Vacation Rentals
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Exceptional(18)

$1113.38

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Private Vacation Home

Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr

Lakeside, Michigan, United States

Summary:brbrSumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard.brbrbrbrThe Space:brbrClassy, awe-inspiring, and sumptuous, this 1928 4 BR/2.5 BA vacation home, located just a block from Lake Michigan in “Harbor Country,” was once a local retail gathering place. Recently refurbished into a stunning residential home, it includes gorgeous reclaimed flooring from antique beams, custom doors, light fixtures, and hardware, as well as top-of-the-line plumbing fixtures.brbrbrbrThe kitchen-dining room-living room area—a massive, superbly well-lit space—features entire walls of French windows, original glass-block, and a wide array of seating options for meals: 4 chic stools at the white marble island, 4 leather seats around a circular marble coffee table, and a 10-seat reclaimed wood dining table. The beautifully lit living room has a classic stone fireplace at its center, stylish (yet ultra-comfortable) couches and chairs, and a wide-screen TV.brbrbrbrIn addition to the three bedrooms and bathrooms on the ground floor, there’s a second-floor sleeping loft, perfect for kids with cute bunk beds and a real (mini) teepee. All bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and your guests. Black Door Bungalow can sleep up to 10.brbrbrbrMAIN FLOORbrbrPrimary Bedroom: 1 King bedbrbrBedroom 2: 1 Queen bedbrbrBedroom 3: 1 Queen bedbrbrbrbrUPSTAIRS FLOORbrbrBedroom 4: Full-over-full bunk bed that sleeps 4brbrbrbrAnother “extra” is the detached garage, which has been turned into a posh game room, with high-end shuffleboard and foosball tables, a big-screen TV, and a sound system. The exterior—featuring a spacious covered patio with cozy rattan couch, chairs, and a 4-seat dining table, leading to a bluestone courtyard—has been extensively landscaped with lush plantings, trees, and professional lighting. The home also includes a high-end kitchen, EV charger, and laundry appliances.brbrbrbrIn addition to being an easy walk from a majestic, crystal-sand Lake Michigan beach—and a super-short drive to popular beaches like Pier Street Beach and Cherry Beach—you and your guests can also enjoy the many activities afforded by being near Warren Woods State Park, which offers all sorts of woodland hiking and biking trails. The region’s largest recreational harbor provides countless water-related excursions and rentals, from fishing trips to boat, kayak, jet-ski, and paddleboard rentals, as well as day and evening cruises. There’s also the Acorn Theater, a local treasure for live performances by nationally recognized music artists, and a number of nearby breweries, wineries, brew pubs, and even an award-winning distillery for you to check out. Of course, you and your guests can also enjoy sampling to your heart's content the many popular restaurants, cafes, art galleries, boutiques, and antique shops just a hop, skip, and a jump away in Union Pier and downtown New Buffalo.brbrbrbrThe Neighborhood:brbrJust 75 miles from downtown Chicago, New Buffalo/Lakeside is the gateway to Michigan and a historic Lake Michigan beach town. There are plenty of shops, places to eat, and recreational offerings. Beyond the legacy of summer fun, find a community of hosts and creatives sharing their love of art, culture, and craft throughout the year. New Buffalo is also the location for Southwestern Michigan’s first gambling casino, the Four Winds Casino Resort, and Silver Creek Event Center – the place for concerts featuring headliner entertainment plus conferences and special events.brbrbrbrGetting Around:brbrWe highly recommend a personal vehicle to get around and explore the local area. There is an Amtrak Station in New Buffalo (225 North Whittaker St.) that offers service to Chicago, as well as Ann Arbor and Detroit. The South Shore Line, another option for a day trip to Chicago, stops in Michigan City, IN about 15 minutes’ drive from the house. brbrbrbrWe will provide you with a helpful virtual guide prior to check-in that showcases a comprehensive list of area eateries, attractions, parks and more.brbrbrbrOther Things to Note:brbrFrom June 4 through August 26, 2026, this home has a 7-day minimum stay policy.brbrbrbrRoad construction is ongoing through the end of spring and the beginning of summer under Chikaming Township direction. brbrbrbrTo ensure a safe and compliant stay, all guests are required to complete identity verification prior to check-in. A valid government-issued photo ID will be collected and verified, and the name on the ID must match the credit card used for payment. When applicable, a background screening may also be required as part of the booking process.brbrbrbrAll guests are required to review and sign Juniper Holiday + Home's Guest Occupancy Agreement prior to check-in. While we understand that events can affect your trip, it is our policy to stick to the agreed-upon cancellation policy in the listing. We recommend purchasing vacation travel insurance if you suspect you may need to cancel your reservation.brbrbrbrThe minimum age to rent this home is 25.brbrbrbrA non-refundable Accidental Damage Waiver is included with your reservation. This waiver covers accidental damage or loss to the rental property caused by you or members of your party up to a maximum of $2,000. This plan does not cover intentional acts, gross negligence, or willful misconduct.brbrbrbrWe welcome up to 3 dogs at this home at no additional charge. Please include the number of pets you plan to bring or let our team know after booking. brbrbrbrOne of the special qualities of the home is its remote setting, though that also means Wi-Fi signal can be less robust than in town. Guests planning to work remotely should keep this in mind, as the connection may not always support a dependable workday. We would be glad to recommend nearby cafes with stronger service.brbrbrbrOut of respect for our staff and their families, we do not permit check-ins or check-outs on Thanksgiving Day or Christmas Day. Thank you for your understanding.brbrbrbrPermit No: STR-25-0003
Bed 4

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Bath 2

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Sleep 10

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Exceptional(56)

$374.49

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Private Vacation Home

Cozy Lakeside Cottage.... with access to a private beach!

Lakeside, Michigan, United States

Escape to the coziest, lakeside cottage. Recently renovated to perfection, this quaint and well-kept 3 bedroom, 2 bath cottage is located on a private road and down the road from a private beach paradise. This property is perfect for couples, families and friends alike as it is a cozy space, yet large enough for privacy. Enjoy cooking in a well equipt kitchen, read a book on the covered porch, walk down the lane to dip your feet in the lake, or enjoy a nice barbecue with a cocktail- your options here are endless. In case you aren't a well suited guest for completely unconnecting, we have the fastest wifi you will ever experience and a cable TV in each room. The house has its own driveway for ample overnight parking and an in-unit washer/dryer for convenience. Complete with air conditioning and heat, your stay here is guaranteed to be enjoyable and comfortable. Our superb location is a stones throw from Union Pier, New Buffalo and Harbert, but nestled in our own friendly, lakeside community. We provide many amenities to make sure your stay is as effortless as possible, after all, life is great at the lake!brbrWe are Family Friendly: We proudly partner with BabyQuip for Baby Gear Rental. Additional information available upon request from owner. Including but not limited to: strollers, wagons, car seats, full size cribs, Snoo's, pack n' plays, highchairs or boosters, toys, baby gates, extra beach gear and much more. We also provide a curated list of recommended activities in our area if the beach isn't calling your name. brbrWe provide the following amenities to make your beach vacation fun and relaxing:br-access to a private beachbr-a fully stocked and renovated cottagebr-baby gear rentalsbr-curated list of recommended activities and restaurantsbr-a grillbr-giant jenga, corn hole, bocce ball, uno, checkers, connect four, playing cards, and morebr-free wifi and cable, free parking
Bed 3

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Bath 2

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Sleep 6

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Exceptional(11)

$1417.98

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Private Vacation Home

Lakeside Escape – Beach Access, Heated Pool, Hot Tub & Sunset Views

Lakeside, Michigan, United States

Welcome to Lakeside Escape, a luxurious lake house just a 3 min walk from a stunning west-facing beach, perfect for enjoying breathtaking sunsets over Lake Michigan. This family-friendly retreat offers a giant yard for outdoor activities including an in-ground heated pool, fire pit, gazebo, and a relaxing hot tub to unwind under the stars. Whether building sandcastles, taking a refreshing dip in the pool, roasting marshmallows, or soaking in the serene sunsets, Lakeside Escape promises an unforgettable vacation for all ages. Your perfect getaway awaits!brbrHighlightsbr- Semi-Private BEACH access is only a 3-minute walk!br- In-ground heated poolbr- Stunning sunsets over beautiful Lake Michiganbr- 6 bed + 4 bath luxury beach house br- Fire pit with Adirondack chairs br- Perfect for family gatherings or a getaway with friendsbr- Large Hot Tubbr- EV charger Level 2br- 2 Kitchens ideal for large gatherings and holiday festivitiesbr- Private in-law suite that can be closed from main living area for privacybr- Apartment with private entrancebr- 2 Cozy gas fireplacesbr- Super comfortable, luxury memory foam bedsbr- 80” smart TV ideal for watching the gamebr- 5.4 miles to downtown New Buffalobr- 90 minutes from Chicago by car or take the train!brbrKitchenbrThe primary kitchen has just about everything a gourmet chef could need to prepare a tasty meal. Outfitted with stainless steel appliances and a 4-burner gas range, there are plenty of tools, appliances, and glassware to cater to your crew. A few notable items include a crock pot, air fryer, blender, Keurig with a selection of Starbucks coffee pods and a standard drip coffee maker. The kitchen has seating for 4 around the island and views of the fireplace and Smart TV in the living room. A gas grill is just outside the kitchen door for all your grilling needs. Second refrigerator/freezer located in the 2nd kitchen in the in-law suite. The 2nd kitchen also includes a 4-burner gas range, microwave, and coffee maker and Keurig. brbrOutdoor SpacebrHead to the semi-private beach to watch the sunset, cool off in the in-ground pool, enjoy a star-lit night in the hot tub, or roast the perfect s'more around the fire pit. *The pool is available from Memorial day to mid-October, inquire for specific dates. Please note that West Michigan gets a lot of snow in the winter so the fire pit and outdoor seating may not be available. brbrMain Living RoombrThis open-concept space is optimal for entertaining. The living room features two over-sized sofas that are so comfortable, you’ll never want to get up. Two-story vaulted windows provide beautiful natural light and an open feel to the space. The gas fireplace will keep you cozy on cold Michigan nights. There is an 80” smart TV for enjoying a family movie or catching the big game. brbrIn-law Suite brLooking for a place to quietly relax Do the kids need an entertainment space of their own The in-law suite features a 2nd kitchen, a full bath with tub/shower combo, and a queen sleeper. This space can be accessed from the main house (it does require that you walk through bedroom #5) or can be accessed through a private entrance off the driveway. The additional living room offers a second gas fireplace and a 50” smart TV for entertainment. brbrBedrooms:br1: Primary suite on the private 2nd floor. King bed with ensuite full bath including soaking tubbr2: 1st floor room with King bed, nearest the 1st floor full bathbr3: 1st floor room with 2 bunk beds (2 twin top bunks and 2 full bottom bunks)br4: 1st floor room (front room) with King bedbr5: 1st floor with King bed in in-law suite. Please note that this bedroom is a pass-through to the in-law suite. The bedroom is connected through a door at the back of the main kitchen. The in-law suite can be accessed through a separate entrance near the garage so this can be made private if needed.br6: Apartment bedroom: This room is a stand-alone apartment that is NOT connected to the main house. Please see the photos of the separate door entry with smart lock (it is within a few feet of the main entrance). There is a single day bed with a single bed trundle (sleeps 2), a private full bath with shower, and a 40” smart TV.brbrBathrooms:br1: 2nd floor primary bedroom ensuite with shower and soaking tub. Please note that the toilet is in a tiny alcove at the back of the bathroom and has a very low ceiling. br2: 1st floor full bath with tub/showerbr3: Full bath located in in-law suite with tub/showerbr4: Full bath located in apartment with standing showerbr*All bathrooms are stocked with shampoo, conditioner, and body wash. 2-3 rolls of TP are provided in each bathroombrbrTraveling with kids brWe provide a pack-n-play, high chair, and kids’ dinnerware to save you the hassle.brbrLaundrybrFull-sized washer and dryer are on the main floor. Detergent is available should you need.
Bed 6

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Bath 4

Bath

Sleep 16

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Exceptional(31)

$238.0

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Cottage

SPRING & FALL DISCOUNT! One Bedroom Cottage with Private Beach!

Lakeside, Michigan, United States

***SPRING & FALL DISCOUNT! When you rent 2 or more nights at Lat's Cottages, you get a third night FREE! This is on top of our already discounted off season rates! Offer good September through May (not valid Memorial Day through Labor Day weekends). brbrWe are located on the relaxing shores of Lake Michigan in Lakeside MI, just five miles north of the Indiana border. brbrOur cottages and Lake House are set on a 2 acre fenced in and landscaped lot with 200 feet of sandy private beach. This VRBO listing is for Cottage #2. brbrThis cottage has one bedroom and can sleep 2 guests. There is a queen bed in the bedroom and a foldout futon couch in the living room. In addition, this cottage includes a private picnic table, lawn furniture, and grill.brbrOn the beach we have a large fire pit, picnic table, beach chairs and umbrellas, assorted beach toys, as well as 4 kayaks and two row boats for our guests to use.brbrA total of 17 guests can be supported between all of our units. Perfect for family reunions or large get togethers! We have been providing memorable vacations to families for over 60 years.brbr***Please note our property is set on a bluff overlooking Lake Michigan. We have approximately 100 stone steps from the yard to the beach. This can be difficult for guests with certain health and joint problems. We do have multiple rest benches along the stairs to take rest breaks.***brbrKeywords: Cottages, Lake Michigan, Private Beach, Family vacation, family reunion, fire pit, large yard, spacious, large groups, cozy cottages, Lake House
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Bath 1

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Sleep 2

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Exceptional(77)

$536.0

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Cottage

Summer Weeks still available! Short walk to a private beach!

Lakeside, Michigan, United States

Rentals available throughout the yearbrbr***Summer Weekly Rentals Saturday to Saturday in June - August*** brbrEnjoy the open floor plan, 3 bedrooms (master and 2 bedrooms) 2 bathrooms, comfortable living room furniture and fireplace. The newly renovated main bathroom now has a deep tub to take away the stress of the city. One block to the private association beach. After a fun day at the beach, you can play in the front yard, relax in the screened porch or soak in the hot tub. Outdoor hot tub can be enjoyed all year long. Washer/dryer and dishwasher.brbrWhether you are coming to enjoy the fresh air, shooting stars or walks on the beach, the Cozy Cottage has a lot to offer. Come to reduce your stress and recharge. br**June 14-September 6 are WEEKLY RENTALS ONLY**brCheck-in: 4:00pmETbrCheckout: 10:30amETbrCleaning Fee: $300brbr*PRIVATE SANDY BEACH ACCESS, less than a block walk and then 50 stairs down*br*Screened in back porch*br*Outdoor hot tub available all year*br*Located less than ten minutes from New Buffalo*br*Farmers market only 2 minutes down Red Arrow Highway, Union Pier, Sat.-Sun.*br*Many restaurants - Whistle Stop, Stray Dog, Haymarket, Redamak's, Beer Church Brewery, and Ghost Isle Brewery*br*Close to wineries*br*Four Winds Casino, New Buffalo and a quick 20 minute drive/uber to Blue Chip Casino, Michigan City*br*Lighthouse Place Premium Outlets is the perfect spot to get good deal at all your favorite stores. Located in Michigan City!! We discovered - Leeds Public House - large outdoor dining area nearby*
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(17)

$271.0

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Cottage

SPRING & FALL DISCOUNT! Two Bedroom Cottage with Private Beach!

Lakeside, Michigan, United States

***SPRING & FALL DISCOUNT! When you rent 2 or more nights at Lat's Cottages, you get a third night FREE! This is on top of our already discounted off season rates! Offer good September through May (not valid Memorial Day through Labor Day weekends). brbrWe are located on the relaxing shores of Lake Michigan in Lakeside MI, just five miles north of the Indiana border. brbrOur cottages and Lake House are set on a 2 acre fenced in and landscaped lot with 200 feet of sandy private beach. This VRBO listing is for Cottage #3. brbrThis cottage has two bedrooms and can sleep 4 guests. One bedroom has a queen bed, while the other bedroom has two twin beds. There are two couches in the living room. In addition, this cottage includes a private picnic table, lawn furniture, and grill.brbrOn the beach we have a large fire pit, picnic table, beach chairs and umbrellas, assorted beach toys, as well as 4 kayaks and two row boats for our guests to use.brbrA total of 17 guests can be supported between all of our units. Perfect for family reunions or large get togethers! We have been providing memorable vacations to families for over 60 years. brbr***Please note our property is set on a bluff overlooking Lake Michigan. We have approximately 100 stone steps from the yard to the beach. This can be difficult for guests with certain health and joint problems. We do have multiple rest benches along the stairs to take rest breaks.***brbrKeywords: Cottages, Lake Michigan, Private Beach, Family vacation, family reunion, fire pit, large yard, spacious, large groups, cozy cottages, Lake House
Bed 2

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Bath 1

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Sleep 4

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Exceptional(67)

$418.33

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Cottage

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside, Michigan, United States

**** IMPORTANT - PLEASE READ ****brbr**** RATES FOR FALL, WINTER, SPRING SEASON RENTALS ARE FOR ONE (1) COTTAGE****brbr**** SUMMER SEASON WEEKLY RENTALS between June 20 and August 29, 2026 ARE FOR BOTH (Except for special circumstances which will be indicated below this paragraph) ****brbrGroup size cannot exceed 20 including children for both cottages. An additional housekeeping fee of $175 will be required in addition to the $175 already shown when reserving 2 cottages.brbrRate quotes for Fall, Winter and Spring and early Summer (May 29 - June 19) dates (not including holidays) automatically generated by this site include a base rate for up to 2 people in one cottage. If your group size exceeds 10 you will need to rent both cottages and will require a custom quote. Custom quotes are not automatically generated by vrbo. The vrbo site only generates a quote for one cottage during the Fall, Winter and Spring Seasons. If your group size exceeds 10 people or you prefer both cottages, request a quote instead of using the book now feature. When there are more than 2 people, there is an additional guest fee of $30 per person/night. When the group size exceeds 10 people, a custom quote can be provided that includes the additional cottage and housekeeping fee.brbrPlease note that this site does not always indicate availability for both cottages. It is best to call or check with us to confirm availability. Check our availability calendar at LakesideBeachHouse com.brbrGuests who stay at the Beach House at Lakeside, Mi. have their choice of renting one or two cottages. Each cottage has 4 bedrooms and 2 baths. We allow no more than 10 people per cottage. Our rental rate structure will suit groups of 2 to 10 people in one cottage and up to 20 people in both cottages.brbrPosted Rates are for 1 (one) cottage except during the Summer Weekly season when availability is limited to guests who agree to rent both cottages for 7 nights. Our Summer weeks go Saturday to Saturday. Our posted Summer Season Rates are for both cottages for 7 nights.brbrSince the cottages can be reserved either together or separately, a date indicating availability on the vrbo calendar may NOT always mean both cottages are available. Inquire before you reserve.brbrOur tastefully decorated, fully furnished, cottage homes are located just off the shores of Lake Michigan. The property offers alternatives to the beach with a heated swimming pool (for summer guests - Memorial Day to around Mid September) and an outdoor hot tub (for Spring, Winter, and Fall guests - around Mid September (after pool is closed) to prior to Memorial Day weekend) with outdoor pool decks, lounge chairs, and beautifully landscaped grounds featuring two outdoor patios. Available parking will accommodate up to 8 cars.brbrA short 200 yard walk takes you from the front door to the beautiful ocean-like sandy beach where you can walk for miles along the shoreline. Visit our Website for complete detailed information including Photos, Floor Plans, Area Maps, Rates, and Current Availability.brbrLakesideBeachHouse combrbrNote that our availability calendar may not be up-to-the-minute accurate since we take reservations from several different sources. If you have 11-20 people you will need 2 cottages. If you have 10 or fewer people and prefer 2 cottages, you will receive a custom quote from us. Quotes generated from this site are for one cottage except for summer season rentals which automatically include both cottages beginning the 2nd full week of June. You must inquire or go to our website for current rates and availability. Pets and animals are an additional $10/animal/night.brbrThe Beach House at Lakeside, Michigan has been a popular vacation Rental for hundreds of Families for over 30 years. Just a 90 minute drive from Chicago and you and your family or friends will have arrived to a place not just on the other side of the Great Lake but a world away from what you encounter every day. In Lakeside Michigan, you are in a small town that is part of family of beach town communities known as Harbor Country. New Buffalo, Union Pier and Grand Beach are among the neighboring towns.brbrWhile frequented for decades by Chicagoans who both vacation here and own second homes, thousands from all over the Midwest and other parts of the country make this area part of their summer every year. Yet when you are in Lakeside, you would never know that others travel many miles to come here too. Now, you too can partake in the laid back beach town experience when you stay a summer week at the Beach House at Lakeside, Michigan.brbrAt the beach House, you have a choice of renting one or two fully furnished units. Each unit will comfortably accommodate up to 10 people and has 4 bedrooms, 2 baths, fully equipped kitchen, dining room and Sunroom.brbrAfter you have arrived and settled in, you will no doubt take the short 200 yard walk to the private beach to witness to one of the most impressive sunsets found anywhere on the planet. It is the main attraction of this vacation destination. And on a day when you need a break from the sun and the waves, you can still enjoy a refreshing swim in a heated pool or pedal a bike along the miles of trails that meander through the neighboring towns, forests, farmlands and wine country. brbrWith outdoor patios in the front garden, and back yard, you also have ample seating around the pool for sunbathing or having lunch. At meal time, you have many options to explore. In addition to grilling on the Weber, you will discover the areas many first rate restaurants, a famous burger joint, ice cream shops and cafes.brbrWhen you seek some variety, there are the many antique shops along Red Arrow Highway, Golf courses, Fruit picking, art galleries, shopping, the Warren Dunes State park and even a first class Casino in nearby New Buffalo.brbrWhen the summer season winds down, the fun continues. With the Fall Season, the area becomes flush with color and beauty. After the pool gets closed for another year, we open our outdoor hot tub for our fall and Winter Guests. Some of you might come for a girls Only weekend or cheer on the Fighting Irish of Notre Dame in nearby South Bend.brbrRegardless of whether you come for a summer week, or a Spring, Fall or Winter Weekend, you will leave having just experienced some unforgettable memories along the shores of Lake Michigan when you’ve stayed at the Beach House at Lakeside.brbrKeywords: cottage near beach, beach house, Union Pier Rental, New Buffalo Rental, Michigan Vacation Rental, Michigan Vacation Rentals, michigan cabin rental, michigan lake vacation rental, michigan cottages, brmichigan cabins, michigan cottage rental, michigan rental vacation, LakesideBeachHouse, brmichigan resorts, michigan rentals, brmichigan lake rental, michigan cottage rentals, michigan vacation cabins, michigan vacation ideas, southwest michigan vacation rental
Bed 8

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Bath 4

Bath

Sleep 20

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Exceptional(21)

$265.0

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Cottage

SPRING & FALL DISCOUNT! Two Bedroom Cottage with Private Beach!

Lakeside, Michigan, United States

***SPRING DISCOUNT! When you rent 2 or more nights at Lat's Cottages, you get a third night FREE! This is on top of our already discounted off season rates! Offer good September through May (not valid Memorial Day through Labor Day weekends). brbrWe are located on the relaxing shores of Lake Michigan in Lakeside MI, just five miles north of the Indiana border. brbrOur cottages and Lake House are set on a 2 acre fenced in and landscaped lot with 200 feet of sandy private beach. This VRBO listing is for Cottage #1. brbrThis cottage has two bedrooms and can sleep 4 guests. One bedroom has a queen bed, while the other bedroom has two twin beds. In addition, this cottage includes a private picnic table, lawn furniture, and grill.brbrOn the beach we have a large fire pit, picnic table, beach chairs and umbrellas, assorted beach toys, as well as 2 kayaks and two row boats for our guests to use.brbrA total of 17 guests can be supported between all of our units. Perfect for family reunions or large get togethers! We have been providing memorable vacations to families for over 60 years. brbr***Please note our property is set on a bluff overlooking Lake Michigan. We have approximately 100 stone steps from the yard to the beach. This can be difficult for guests with certain health and joint problems. We do have multiple rest benches along the stairs to take rest breaks.***brbrKeywords: Cottages, Lake Michigan, Private Beach, Family vacation, family reunion, fire pit, large yard, spacious, large groups, cozy cottages, Lake House
Bed 2

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Bath 1

Bath

Sleep 4

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Exceptional(111)

$400.0

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Cottage

Short walk to the beach & backs up to the woods! Few dates left - May June Sept

Lakeside, Michigan, United States

brA Perfect Get Away on a peaceful lane!brBlue Bird Cottage in Lakeside, Michigan. brbrRATES: April 2026 - $375/nightbr taxes and cleaning fee includedbr minimum 2 night staybrbrRATES: May 2026 - $375/nightbr taxes and cleaning fee includedbr minimum 2 night staybrbrRATES: June 2026 - $400/nightbr taxes and cleaning fee includedbr minimum 2 night staybrbrRATES: July - Aug 2026- $425/nightbr taxes and cleaning fee includedbr minimum 3 night staybrbrRATES: Sept 2026 -$400/nightbr taxes and cleaning fee includedbr minimum 2 night staybrbrRATES: Oct 2026 - $350/nightbr taxes and cleaning fee includedbr minimum 2 night staybrbrbrbrNOTE: 3 night minimum for Memorial Day holiday weekend, and July through Labor Day holiday weekend.brbrbr**Additional charges may apply, up to owner discretion.br**Prices may change due to Owner discretion.br**SECURITY DEPOSIT REQUIREDbr** Maximum 2 dogs. A third dog will be charged an additional $100.00 paid directly to Owner.brbrLocated on a very peaceful, wooded lot-- Wake up and maybe see a deer in the woods behind the house and the sound of the birds singing. On a windy day, you can hear the waves from Lake Michigan! brbrA charming and relaxing home in Lakeside, MI, only ten minutes to the shops/dining/entertainment of New Buffalo! brbrA short 7 minute walk to the quiet/private Association beach of Lake Michigan. Only for owners and guests.brbrPlenty of trails for hiking, bird watching and biking within minutes from the property. This area is gorgeous in spring, summer, fall, and winter!brbrLocation from Chicago is only 1 hour and 30 minutes from downtown - an ideal weekend escape to get away from the hustle and bustle of the city! brbrThe home is irresistibly charming and comfortable. All linens and towels are provided, as well as all cooking utensils for great at-home meals and barbecues! We provide charcoal, firewood for the fire pit, coffee and filters! brbrFree Wi-FI, Satellite TV, VCR/DVD, washer/dryer.brbrThe home also has a large private yard (fenced in ONLY at the front of the yard, the remaining yard is surrounded by woods and landscaping) perfect for children & pets. The neighborhood is very child safe and pet friendly. The house has games, books, puzzles, and satellite TV.brbrDon't leave your dog at home! We DO Allow DOGS, but no cats.(Pets are considered on an individual basis). So, if you are averse or allergic to animals, this is NOT the home for you.brbrABSOLUTELY NO SMOKING IN THE HOUSE. brbrWe do not rent to anyone under 25.brbrPLEASE NOTE -- most all of the homes in the area have access the Association beach via the 55 stairs, down to the beach area.brbrKeywords: Modern Country Vacation Home
Bed 3

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Bath 1

Bath

Sleep 6

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Exceptional(8)

$450.0

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Private Vacation Home

SPRING & FALL DISCOUNT! Updated Lake House with Private Beach!

Lakeside, Michigan, United States

***SPRING & FALL DISCOUNT! When you rent 2 or more nights at Lat's Cottages, you get a third night FREE! This is on top of our already discounted off season rates! Offer good September through May (not valid Memorial Day through Labor Day weekends). brbrWe are located on the relaxing shores of Lake Michigan in Lakeside MI, just five miles north of the Indiana border. brbrOur cottages and Lake House are set on a 2 acre fenced in and landscaped lot with 200 feet of sandy private beach. This VRBO listing is for The Lake House. brbrThis two story house has two bedrooms and can sleep 6 guests. One bedroom has a queen bed and cot and the other bedroom has two twin beds and a cot. The downstairs living area is a great room with an open concept perfect for entertaining and large groups. In addition, the Lake House includes a private picnic table, lawn furniture, and grill.brbrOn the beach we have a large fire pit, picnic table, beach chairs and umbrellas, assorted beach toys, as well as 4 kayaks and two row boats for our guests to use.brbrA total of 17 guests can be supported between all of our units. Perfect for family reunions or large get togethers! We have been providing memorable vacations to families for over 60 years. brbrCheck out our other VRBO listings on the same property here:brbr***Please note our property is set on a bluff overlooking Lake Michigan. We have approximately 100 stone steps from the yard to the beach. This can be difficult for guests with certain health and joint problems. We do have multiple rest benches along the stairs to take rest breaks.***brbrKeywords: Cottages, Lake Michigan, Private Beach, Family vacation, family reunion, fire pit, large yard, spacious, large groups, cozy cottages, Lake House
Bed 2

Bed

Bath 1

Bath

Sleep 6

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Exceptional(14)

$858.27

/ Nightly
Private Vacation Home

Relax on your own private beach on stunning Lake Michigan

Lakeside, Michigan, United States

FULLY RENOVATED HOME, PRIVATE LAKE MICHIGAN BEACH, LAKE VIEWS, SUNSETSbrbrCome and bring your family and friends. Swim and play on your own huge private beach. Enjoy sunsets on the beach or up on a high bluff.brbrThis secluded, four-season, home sits on a bluff in Lakeside. It has been freshly renovated with open living areas designed to accommodate a group gathering. Living room with new OLED TV, woodburning fireplace, sectional couch and chairs. The dining table seats eight and can be extended for up to 10, which can serve double-duty for WFH, puzzles, cards or board games.brbrLarge, bright kitchen is fully stocked for big breakfasts and evening meals. Huge center island with stools, 36” dual-fuel Bertazzoni range, two sinks and super-quiet Bosch dishwasher. Includes toaster, Ninja blender, hand mixer, electric kettle, cookware, coffee pot, built-in microwave.brbrYou can lounge, dine and enjoy views of the lake and beautiful sunsets from the large back deck and yard. The outdoor fire pit is at the edge of the bluff and also overlooks the lake. Just beyond the fire pit are the stairs to the beach. brbrYou’ll have your own private beach with the gear you need in the shed down at the beach — beach chairs, umbrellas, inflatable water hammocks and some toys for the beach and lake. There are about 120 steps to the beach (no need for a Stairmaster!), and there is a stopping point and lookout about halfway down.brbrFour bedrooms sleep 10. Two bedrooms have queen-size beds, one has a queen bunk bed, and one has a twin bunk. All the beds are new and guests have remarked about how comfortable those are. brbrThere are two full bathrooms. One features a tub-shower combo and has an electric towel warmer.brbrHome is about .3 miles walking distance to the Union Pier Whistle Stop and Red Arrow Roadhouse. It's a few minutes drive to Union Pier Market and Flagship Fish Market. Short drives (less than 10 minutes) to Sawyer, New Buffalo and Three Oaks. brbrCook at home or enjoy dozens of local restaurants in Harbor Country: Red Arrow Roadhouse, Timothy’s, Gather, Skip’s, Union Pier Social. Check out the area’s breweries and distilleries, including Seedz, Beer Church, Ghost Isle, Greenbush, Haymarket and Journeyman.brbrAvailable year-all round for fall, winter or spring getaways. Have an indoor fire in cooler weather or an outdoor fire all summer. Jacuzzi is located on the back patio and kept hot all year long. There are plenty of fall cool weather activities, apple orchards, cross country skiing, wineries and more.
Bed 4

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Bath 2

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Sleep 10

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Exceptional(17)

$543.54

/ Nightly
Private Vacation Home

Fantastic family home near the lake with WiFi and large deck

Lakeside, Michigan, United States

Friendly FarmsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAbsolutely fantastic both inside and out, Friendly Farms is more than ready to assist in making the best memories mere minutes from the clear waters of Lake Michigan! With a wooded surrounding, this home offers natural privacy, and the exterior is reminiscent of a classic farmhouse, allowing everyone to slip into the simpler lifestyle in no time. Step inside, and you will be greeted by the breathtaking interior featuring colorful decor, high-end furnishings, and an open layout that will be absolutely perfect for mingling and entertaining after a full day of adventure. When everyone wants a bit of fresh air, the front porch, back deck, hot tub, and firepit area with Adirondack chairs can all accommodate guests as the sun goes down. Plus, the well-equipped kitchen right inside will come in handy when appetites are high so bring along a few recipes to whip up using the high-end appliances provided! With so much fun just waiting to be had, what are you waiting for The lake lifestyle is calling!brbrThings to KnowbrFree high-speed WiFibr*A cat spends time at this home on occasion (not full time)brThis property is managed by Vacasa Michigan LLCbrbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 28 years of age to book. Guests under 28 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 3

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Bath 3

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Sleep 6

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Exceptional(6)

$557.99

/ Nightly
Private Vacation Home

Stylish & Well-Equipped Home with Private Outdoor Pool, WiFi, Deck, Gas Grill

Lakeside, Michigan, United States

Butterfly Pool HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLight and airy, relaxed but stylish, Butterfly Cottage is a great place to get away from the city! There is a huge, fenced back yard with a sparkling private pool, a big lawn for games and sports, and a large deck from which to view it all. Best of all, Pier Street Beach in Lakeside is exactly one mile from the house so you can walk, bike, or drive to the beach as there is a tiny bit of roadside parking allowed.brbrThe house has an open, flowing layout and big windows that let the sunlight in. There‚Äôs a fireplace in the living area and a den where you can kick back and watch TV. The well-equipped kitchen has a pass-through to the dining room, which comfortably seats eight. There are three bedrooms on the upper level, beginning with the main bedroom suite that features a king bed. The main bathroom has a deep soaking tub and two additional bedrooms that share a full bathroom. There are another full bathroom and bedroom with a queen bed on the main level that is great for those who can't do a lot of stairs. There is also a large finished family room in the basement.brbrThere are plenty of other sources of adventure and entertainment close by, including the Four Winds Casino, great restaurants, art galleries, and interesting stores to explore. Butterfly House is in a peaceful country location on the east side of Red Arrow Highway but still close to the lake, with woods across the road and neighbors a discrete distance away. All the amenities and opportunities of Harbor country are right here so come and enjoy some pool time at this inviting house!brbrTHINGS TO KNOWbr*Please note that the pool is open from roughly May 15 - September 15 every year.brbrThe pool is open from Memorial Day through Labor Day. The pool will be heated to 80 degrees prior to your arrival. If you wish for the heat to increase, please contact Vacasa after you secure your booking. The cost for additional pool heat is $25/night.brbrThis property is managed by Vacasa Michigan LLC.brbrParking notes: There is free parking available for 3 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 5

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Bath 4

Bath

Sleep 8

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