Home Vacation Rentals By Owner In Lakeside, MI

Showing 40 Of 65 Vacation Rentals
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Exceptional(53)

$988.5

/ Nightly
Country House

Contemporary Farmhouse, 4200 sq ft on 9 acres with private neighborhood beach.

Lakeside, Michigan, United States

br4200sq/ft 6 bedroom, 2 half baths, 2 spacious full baths and outdoor shower, contemporary Farmhouse. On 9 acres with walking trails and short walk to association beach, beach passes included. Located in the heart of Lakeside, Harbor Country. Perfect for family reu.brbrbrThis is an owner managed property. July and August available for weekly rentals Sunday to Sunday only.. All other dates 3 day minimum. Open style vacation house. Living/dining, and gourmet kitchen with fully equipped, pantry, Garland 6 burner industrial stove .Loved by gourmet cooks and spacious for a large crowd. Table with seating for 12 and nearby kitchen island seating an additional 5.br BBQ on deck with outside dining. Perfect for entertaining, large and small gatherings. Separate comfy TV room, located in air conditioned bedroom wing. Screened in porch, hot tub, fenced in yard area for pets.brbrHouse sleeps 14, has 6 bedrooms total, Two very large bathrooms, two half baths, one enclosed private outdoor shower.brbrBedrooms are divided this way... upper level 2 bedrooms, one queen the other king (this room has a small balcony), Large shared bathroom with large walk in shower. Both bed rooms are air-conditioned.brbr First floor bedroom wing has four bedrooms, One king bed, two queen beds and one with double bunkbeds. one very large bathroom with big walk in shower and an additional half bath, all bedrooms have their own door opening up to shared deck that has an enclosed outdoor shower, screened in porch and hot tub. brbrIt is a really fun layout for a large group of people!brbrAssociation beach is a short 5-10 min walk to Lake Michigan and requires a gate pass. 2 gate passes includedbrbrFew items to take note:brProperty is located over private railroad crossing, typically 2 Amtraks and a freight train or two will pass a day. Caution needs to be taken when crossing by looking both ways always.brbrThere is central air in the bedroom wing and window units in the 2 bedrooms in main house. The living room and kitchen have no air conditioning. there are 3 ceiling fans and cross breeze screened doors to decks.brbrKitchen is equipped with a Garland industrial stove, walk in pantry, lots of counter space, its a large fun kitchen to cook in.brbrOutside property has a fire pit, and 9 acres of trails to enjoy through the woods. Part of the front yard is fenced in for pets.brbrJuly and August are only available for full week rentals, Sunday to Sunday. 3 nights minimum any other dates.brbrPlease feel free to contact us for additional information. This is truly one of a kind property.brbrHouse has heated floors for winter and fall retreats. Yoga retreats being offered several weekends through outbrthe winter months. Please call or email for info.brbrOffering winter rates ( 20225) 25% discount on 3 or more nights. Enjoy a cozy fireplace with plenty of wood, walks on a quiet, majestic Lake Michigan beach, nearby restaurants, cross country skiing on property and other local trails. brbrKeywords: Contemporary Farmhouse/neighborhood beach
Bed 6

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Bath 3

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Sleep 14

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Exceptional(44)

$381.5

/ Nightly
Private Vacation Home

Experience Tranquility at Dunedin Cottage:The Perfect Retreat in Harbor Country!

Lakeside, Michigan, United States

Our charming 2-bedroom, 2-bathroom cottage in Lakeside, Michigan offers a delightful retreat for up to 8 guests. Located in the beautiful southwest region of the state, it is conveniently close to Cherry Beach, Townline Beach, and Harbert Beach. Additionally, popular destinations such as New Buffalo, Sawyer, Union Pier, and St. Joseph are easily accessible, ensuring you have a variety of activities and dining options to explore.brThe cottage boasts a tastefully decorated interior, with attention given to every detail. The warm and inviting living room features a cozy gas fireplace, creating a perfect atmosphere for relaxation. If you enjoy cooking, you'll love the designer kitchen, which is fully equipped with all the amenities you need to prepare delicious meals and set a beautiful table.brSleeping arrangements include a spacious main bedroom with a king-sized bed and a second bedroom furnished with a queen-sized bed and a twin bed. The pull out sofa in the living room is a queen bed and the sofa off the kitchen is a twin, The home boasts 2 full baths, 1 with a tub and the other a shower. The cottage also features a fantastic outdoor area, including an outdoor shower, a large grill connected to mains gas, a fire pit for cozy evenings, and a wraparound deck with outdoor furniture and dining table.. For added convenience, there's a whole house generator to ensure uninterrupted power supply.brOn balmy summer evenings, you can enjoy the beauty of the outdoors from the fully enclosed screened porch. If you're a beach lover, the cottage is just 2.5 blocks away from Pier St. Beach, which has recently reopened with new steps, offers a picturesque setting for sunset viewing. Please note that the beach size may vary depending on the day.brWhether you're planning a romantic getaway, a family vacation, or a group retreat, our cottage provides an ideal setting. A minimum rental period of 3 nights is required.
Bed 2

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Bath 2

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Sleep 8

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Exceptional(8)

$1223.07

/ Nightly
Private Vacation Home

Near New Buffalo • Lakeside Retreat w/ Private Heated Pool • Walk to Beach

Lakeside, Michigan, United States

Renovated Lakeside Escape • Near New Buffalo • Private Heated Pool • brWalk to BeachbrbrWelcome to your fully renovated Lakeside retreat — a modern, comfortable 4-bedroom, 2-bath home with a private heated pool, set on a peaceful wooded lot and just minutes from New Buffalo, Union Pier Beach, and the best of Harbor Country. Sleeps up to 10 and designed with families and groups in mind.brbrModern, Fresh Interiors With Room to Spread OutbrbrEvery part of the home has been thoughtfully updated — new furnishings, stylish finishes, upgraded lighting, and a clean, modern feel throughout. The layout is ideal for two families, couples, or multi-generational groups:brbrBedroomsbr*Primary Bedroom – queen bed, modern décor, and plenty of natural lightbr*Bedroom 2 – queen bedbr*Bedroom 3 – full bedbr*Bunk Room – 2 full beds on the bottom + 2 twin beds on top (4 total beds), perfect for kids or cousins’ sleepover nightsbr*Two Hangout / Living Areasbr*Main Living Room – comfortable modern furniture, large TV, bright and airybr*Second Lounge Area – great for kids, games, or relaxing away from the main spacebrbrBoth areas have a clean, stylish, updated feel and give groups the ability to hang out together or spread out when needed.brbrEat-In Kitchen - A renovated, fully stocked kitchen with:brbrFull dining areabr*Updated appliancesbr*Bright, modern cabinetrybr*Everything you need for family meals and grilling daysbrbrPrivate Backyard Oasis With Heated PoolbrYour own quiet, tree-lined outdoor space includes:br*Brand-new heated pool (Memorial Day–Labor Day)br*Spacious modern patio with a large contemporary fire tablebr*BBQ grillbr*Lounge chairs and umbrellasbr*Plenty of room for kids to run and playbrbrIt’s peaceful, private, and often becomes everyone’s favorite part of the stay.brbrWalk to the Beach • Minutes to New BuffalobrbrThe home offers privacy but is close to everything:br*Walk to the beach via the improved Red Arrow pathwaybr*2 minutes to Union Pier Beachbr*Short drive to New Buffalo shops, restaurants, breweries, and marinabr*Close to wineries, Warren Dunes, golf, and scenic Harbor Country townsbrbrPerfect for beach days, pool days, and everything in between.brbrDesigned for Memory-Making TripsbrbrFrom the modern furnishings to the flexible layout, renovated interiors, heated pool, and wooded setting, this home is easy to enjoy and hard to leave. Guests love the comfort, the privacy, and how effortless it feels to settle in.
Bed 4

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Bath 2

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Sleep 10

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Exceptional(1)

$810.69

/ Nightly
Private Vacation Home

Gorgeous Lakeside Home With Pool, Hot Tub, And More!

Lakeside, Michigan, United States

3 Bedroom, 2.5 Bathrooms, Sleeps 08brbrPool Open Memorial Day-September 30th!brHot Tub Open Year Round!brbrExperience luxury and relaxation at Fallen Oaks in Lakeside, Michigan — a beautifully appointed 3-bedroom, 3-bathroom vacation rental nestled in the heart of Harbor Country. This private retreat offers the perfect blend of comfort, style, and resort-style amenities, making it an ideal choice for families, couples, or small groups seeking a peaceful getaway near Lake Michigan.brbrFrom the moment you arrive, you’ll be surrounded by serene natural beauty and upscale features designed for total relaxation. Step outside to your own private oasis, complete with a heated swimming pool, a soothing hot tub, a spacious pool house, and a tranquil sauna — all surrounded by lush landscaping and towering trees that offer both privacy and peace. Inside, the home features three spacious bedrooms, three full bathrooms, and a fully equipped modern kitchen, perfect for cooking meals or entertaining friends and family. Comfortable living areas and tasteful decor throughout the home create a warm, welcoming atmosphere for guests of all ages.brbrLocated just minutes from the sandy shores of Lake Michigan, this home is perfectly situated for those looking to explore all that Harbor Country has to offer. Spend your days hiking at Warren Dunes State Park, wine tasting at local vineyards, shopping in nearby New Buffalo, or simply enjoying the quiet charm of Lakeside. Whether you're planning a summer vacation, fall foliage retreat, or cozy winter escape, Fallen Oaks is a year-round destination designed for unforgettable memories.brbrWith its unbeatable location, luxurious amenities, and inviting design, this Lakeside vacation rental is more than just a place to stay — it's a destination in itself. Availability is limited, so book your stay today and discover why so many guests return year after year to this hidden gem in Southwest Michigan.brbrAll the amenities you would expect in a quality rental including private heated pool, hot tub, sauna, internet, ac/heat, washer/dryer, gas grill, outdoor firepit, indoor gas fireplace, and so much more!brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**Minimum Age of 25 Years Old To Rentbrbr**Maximum Four Car Parking
Bed 3

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Bath 2

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Sleep 8

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$643.95

/ Nightly
Private Vacation Home

Within walking distance to Lake Michigan, beach access, nice patio, W/D & WIFI

Lakeside, Michigan, United States

Summary:brbrFour Bedrooms & a BeachbrbrbrbrThe Space:brbrLocated just a few blocks from the picturesque shores of Lake Michigan, this charming house in Lakeside, MI, offers the perfect retreat for all seasons, being just walking distance away from Orchard Beach! Whether you're into summer water activities like boating, fishing, paddleboarding, and water skiing, or prefer the winter delights of ice fishing and ice skating, this home is ideally situated for all your outdoor adventures. Step inside this cozy abode to find a well-appointed interior featuring a King Bed, Queen Bed, Double Bed, Twin Bed, and Bunk Bed, ensuring comfortable accommodations for the whole family. Enjoy modern amenities such as Netflix streaming, TV, and free WiFi, making it easy to unwind after a day of exploring the local area. The updated back patio provides a large fenced-in yard, which is a lovely space to relax and soak in the serene surroundings or fire up the gas grill for a nice meal, while the fully equipped kitchen with a fridge, stove, oven, dishwasher, microwave, and coffee maker allows you to prepare delicious meals during your stay. With a wood stove for cozy evenings, central AC for warm days, a washer/dryer for convenience, and all linens and towels provided, this home offers everything you need for a stress-free vacation. Explore the charming town of Lakeside with its local eateries, arts, and entertainment options, or venture out to discover the array of attractions in the area. Whether you're seeking a summer getaway or a winter wonderland retreat, this family-friendly house is the perfect home base for your Lakeside adventure. Book your stay now and create unforgettable memories in this lovely Lakeside retreat!
Bed 4

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Bath 2

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Sleep 12

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$399.84

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Private Vacation Home

Dog-friendly cottage with private beach, screened porch, wood fireplace & AC

Lakeside, Michigan, United States

Summary:brbrLake Michigan AdventuresbrbrbrbrThe Space:brbrWelcome to where relaxation meets convenience! This cute small cottage is the perfect choice for a friends' trip, couples retreat, or family vacation. Walk only 1,000 feet to reach Sunset Lane Association Beach, a private association beach for the immediate neighborhood only that also allows dogs. Located in the cute lakefront town of Lakeside, this ground-floor home is surrounded by beautiful trees and lush nature, offering a true 'get away from it all' feeling. Inside, an open floor plan seamlessly combines the living and dining areas and the well-appointed kitchenette. Snuggle up on any of the sofas by the wood-burning fireplace and stream a favorite movie or series on the smart TV. When mealtime comes around, the kitchenette will have your back with all the essential appliances needed to whip up everything, from full-course meals to quick snacks on the go. You can choose to dine indoors or delight yourself with nature in the outdoor dining area on the patio. There is a beautiful screened porch with comfortable seats that leads to the patio. bTHINGS TO KNOW/b There are four backpack beach chairs and an umbrella. Streaming is available using your own accounts. The fireplace is available in the non-summer months. One non-aggressive, non-shedding 40 lb. dog allowed. Kitchenette with a fridge, apartment-size stove and oven, microwave, and coffee maker. No dishwasher. This property is managed by Vacasa Michigan LLC.
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Bath 1

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Sleep 4

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$735.07

/ Nightly
Private Vacation Home

Fully-renovated lakefront home with beach cabana, association beach, & firepit

Lakeside, Michigan, United States

Summary:brbrThe Gatehouse on Orchard BeachbrbrbrbrThe Space:brbrWith a gorgeous top-to-bottom renovation that was completed in 2020 and sporting new updates for 2023, this lakefront cottage in the heart of historic Lakeside is truly one of a kind. This modern home is situated on a mid-size bluff above Orchard Beach, a wide, 80-foot stretch of sand that's shared by association members only at the north end of a long, walkable beach on a natural cove of Lake Michigan. Enjoy access to a private beach cabana, with easy access to chairs, umbrellas, and beach toys to make your excursions on the shores truly memorable. This contemporary home is full of style and natural light, offering new appliances and fixtures throughout, an open and airy great room, and a fully equipped kitchen with an extra-large island and stainless steel appliances - all of which contribute to the authentic, beach-house ambience. Come home from the lakeshore each afternoon to rinse off the sand in the refreshing outdoor shower, get the gas grill going on the raised deck, or simply play with your kids in the spacious yard. Leave your swimsuits to spin in the private washer/dryer, and spend the evening hours telling stories in the warmth of the firepit outside. bTHINGS TO KNOW/b There are 60 stairs leading down to the beach. An outdoor shower is available. Four beach chairs are provided. Board games and a yard bag game are provided. This property is managed by Vacasa Michigan, LLC.
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Bath 2

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Sleep 8

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Exceptional(6)

$951.65

/ Nightly
Private Vacation Home

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

Lakeside, Michigan, United States

Summary:brbrButterfly Pool HousebrbrbrbrThe Space: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. The house has an open, flowing layout and big windows that let the sunlight in. There’s 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. There 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! bTHINGS TO KNOW/b *Please note that the pool is open from roughly May 15 - September 15 every year. The 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. This property is managed by Vacasa Michigan LLC.
Bed 5

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Bath 4

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Sleep 8

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$314.59

/ Nightly
Private Vacation Home

Garden-style cottage with easy beach access, screened porch & small yard

Lakeside, Michigan, United States

Summary:brbrPainted Porch CottagebrbrbrbrThe Space:brbrWelcome to the Painted Porch Cottage, a garden-style cottage in residential Lakeside, Michigan. Fully equipped, this rustic cottage is just two blocks from a private sandy beach. When you aren't playing in the sand, a short car ride will lead you to numerous antique stores, farmers markets, wineries, u-pick farms, outdoor recreation rentals, and delicious dining options. Inside the Painted Porch Cottage, the cozy ambiance is abundant! The bright living room offers a lovely space to sit and watch TV. Steps away, the quaint kitchen provides a pleasant space to play chef and dine with your loved ones. When you aren't eating here, the charming dining room is perfect for family-style meals. Additional hangout spaces include the screened-in porch and the grassy yard with a barbecue grill. Before crawling under the bedroom's quilts, throw your swimsuits in the private washer/dryer for a refresh, and tune the central air-conditioning to your liking. WiFi access and an after-beach outdoor shower round out the cottage's perks. bThings to Know/b Check-in time: 4:00 PM Check-out time: 10:00 AM The fireplace is not operational. All guests shall abide by The Good Neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. Subletting of the Painted Porch Cottage is not allowed. The cottage is a duplexed house and the owners with kids and a dog may stay in the second unit during your stay. This property is managed by Vacasa Michigan LLC
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Bath 1

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Sleep 4

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Exceptional(3)

$1233.88

/ Nightly
Private Vacation Home

Lakeside Home With 40 FT of Private Beach!

Lakeside, Michigan, United States

5 Bedrooms, 2.5 Bathrooms, Sleeps 10brbrLocated in the charming town of Lakeside, we welcome you to Gazebo Beach Cottage! This five-bedroom, 2.5-bathroom home is the perfect getaway for your next adventure! This home has 40 feet of private Lake Michigan beach for you to soak up the sun and sand. Relax on the decking by the lake in the chaise loungers or have your coffee in the gazebo overlooking the blue waters. brbrGorgeous screened-in porch is ideal for your family meals or just hanging out together. Dining for ten as well as ample seating. Roast s'mores under the stars in your wood burning firepit or cook your next meal with the gas grill. Wash away the day's sand in your outdoor shower. brbrThe interior of Gazebo Beach Cottage is open and airy throughout. Fully stocked kitchen has everything you need for cooking. Family room with big screen tv and wood-burning fireplace for those cooler fall evenings. Main floor bedroom with queen bed and en suite full bathroom. Interior dining for six as well as a half bathroom. Second floor has four additional bedrooms and a full bathroom. brbrAll the amenities you would expect in a quality rental including internet, cable, central AC, washer/dryer, wood burning fireplace, gas grill, outdoor shower, wood burning firepit, gorgeous screened in porch, private beach access and much more!brbr**All Guests required to sign and return our Guest Occupancy Agreement.brbr**Minimum age of 30 years old to rent.brbr**Dogs considered. Inquire within.brbr**Maximum four car parking.brbr**Please note while this house has private beach access it is not a lakefront home and does not have lake views. There is one other home between this home and lake. brbr**There are 132 stairs to access private beach and gazebo.
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Bath 2

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