Vacation Home Rentals By Owner In Lakeside, MI

$531.14

ASSOCIATION BEACH ACCESS and PRIVATE TENNIS COURT!

Lakeside, Michigan, United States

4 Bedrooms, 3 Bathroom, Sleeps 10brbrNow With Pickleball Court! (Paddles and Balls Included)brbrFor those who want it all in a vacation, welcome to Match Point! This open concept design is the perfect layout for a vacation home. The kitchen, living & dining area all share the same great space, featuring vaulted ceilings and lots of doors and windows for an amazing amount of natural light. Everything is on one floor for easy access, with the 4 bedrooms and 3 bathrooms down the hall, away from the common areas. There is also a sofa sleeper in part of the sectional sofa in the living area. Additional amenities of this home are many, and include a wood fireplace, sauna, private grass tennis court and lots of outdoor deck space. Located in Lakeside, about 3.5 blocks to the private beach, New Circle Beach. Property located on lake side of Red Arrow Highway.brbr**All Guests required to sign and return our Guest Occupancy Agreement.brbr**Minimum age of 25 years old to rent.brbr**Maximum four car parking.

4

Bed

3

Bath

10

Sleeps

$351.33

/ Nightly

Private Vacation Home

Brand New House, Sleeps 8, Private Beach Rights, Hot Tub!

Lakeside, Michigan, United States

Thanks for your interest in our brand new vacation house in Lakeside - which we are very proud of! See you on the beach.brbrThe House:brOur 3 bedroom, 1,800 square foot house sleeps 8 guests comfortably. It features a modern kitchen, spacious living room and dining room. Other features include a washer & dryer, a back patio with furniture, a gas grill, fire pit, Xfinity Internet, and central air conditioning. And of course the we have a HOT TUB - which is scheduled to be delivered in early July (so no photos available yet).brbrThe Beach:brIncludes private beach access rights to the exclusive New Circle Association Beach. It's a 5 to 7 minute walk from the house. Never crowded and always relaxing. Amazing sunsets.brbrThe Neighborhood:brThis is a perfect get-away-from-it-all destination that still has modern amenities within easy reach. Union Pier is just 1.5 miles down the road with shops, an awesome farmers market, and fine dining.

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Bath

Sleeps

$2098.12

/ Nightly

Private Vacation Home

Lakefront Home With Private Beach and Sauna!!

Lakeside, Michigan, United States

6 Bedrooms, 3.5 Baths, Sleeps 14brbrNow With Sauna!brbrThis gorgeous lakefront home with 100 feet of private beach is perfect for your next getaway! This six-bedroom home is perched over Lake Michigan in the lovely town of Lakeside. Beautiful sandy beaches and gorgeous lake in your own backyard! Your group will love the spacious back deck for your outdoor meals. Cook on your gas grill while overlooking the lake. Inside features a open concept tv room as well as a wood-burning fireplace. Reading room has lake views from almost every window. Fully stocked kitchen that leads into dining area with plenty of seating for everyone. Main Floor has a bedroom with full bed and full bathroom across the hall.brbrThe second floor has four bedrooms with two full bathrooms (Jack & Jill). Bedroom #1 is a king bed, bedroom #2 is a queen bed, bedroom #3 are two twin beds, and bedroom #4 is four twin beds. Main floor bedroom #5 with full bed. Lake views and lake breezes from two of the bedrooms including the master bedroom.brbrNow including the brand-new coach house right on Lake Michigan! Including sleeping for two, half bathroom, fridge and ice maker, internet, and more! Gorgeous addition with breathtaking lake views! Coach House open year-round but water will be shut off Nov-March and may be too cold to sleep in late fall/winter. brbrAll the amenities you would expect in a quality rental including internet, cable, central AC, washer/dryer, wood burning fireplace, outdoor firepit, gas grill, new coach house, private beach access and much more!brbr**All Guests Required To Sign Our Guest Occupancy Agreement and Verification Process Required.brbr**Minimum age of 25 years old to rent.brbr**Maximum four car parking.brbr**Please note the coach house sink and ice maker will not be available until May 01st. The rest of beach house fully functional prior to that date.brbr**There are 90 stairs to access private beach.

Bed

Bath

Sleeps

$420.83

/ Nightly

Private Vacation Home

1000 FT to Assn Beach, Cute Cottage, Outdoor Dining

Lakeside, Michigan, United States

Find your cozy escape at Hygge House in Lakeside, a beautifully renovated two-bedroom home just 1,000 feet from a private Lake Michigan beach that lives up to its name. Check in, and enjoy the cozy, calm stress-free settingbrRelax by the fireplace, unwind on the patio with a fire pit, and enjoy games in the spacious fenced yard. Beach chairs, wagon, and grill are provided, making this the perfect year-round retreat for families or couples seeking warmth, relaxation, and pure Harbor Country charm

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Bath

Sleeps

$1051.33

/ Nightly

Private Vacation Home

Stunning home w/Private Association Beach 2 Screened Porches

Lakeside, Michigan, United States

Please read before booking: br**Minimum age requirement of 30 years old br**Signed guest agreement requiredbr**Events, parties and large gatherings are strictly prohibited and could incur fines by local municipalities or removal from propertybrSunday to Sunday rental during peak season- 30+ age requirementbrbrPlease be sure to check out all of Aqua Vacation Rentals 20+ properties located in Southwest Michigan! Our properties are listed on multiple booking sites and rates may vary. brPlease be sure to read all policies before booking.brbraqua Elite Bold Stump Cottage is a newly built home located in Turner Shores Association in Lakeside, Michigan. The home is just 1.5 blocks from a private association beach on Lake Michigan. This neighborhood has so much history which included a peach orchard that became a popular place to pitch a tent in the summer back in the 20th Century. Then eventually lots were sold and cottages were built which is now Turner Shores. Bold Stump Cottage is a two story brand new home which includes top notch furnishings and features 6 bedrooms and 3.5 bathrooms, two screened porches, a large open concept kitchen/dining room, outdoor game room and yard. This home is just steps to the private association beach. The first floor features a living room with a fireplace, den with TV and sectional, an open concept kitchen/dining room with access to the first screened porch and the primary bedroom with a king bed and a beautiful bathroom that includes a walk in shower and large soaking tub. The primary bedroom has it's own private screened porch also. As you make your way to the second floor you will find five bedrooms and 2 full bathrooms. The first bedroom has a queen bed, second bedroom has a king bed, the third bedroom has a queen bed, the fourth bedroom has 2 twin beds and a crib and the fifth bedroom has a queen bed. Other amenities this home features is radiant heat throughout, game room with Foosball and Ping Pong, wine fridge, outdoor shower, gas grill and electric car charger. The private association beach is just a block and a half from the house and has no stairs. Enjoy your fire on the beach after a day at the beach. brbrRestaurants are a short drive from the house as well as the grocery store. The area has so much to explore including antique malls, shops, restaurants, galleries, wineries, breweries, state parks and so much more. We look forward to having you here to experience all this home and area has to offer! Come and make memories that will last a lifetime!brbrPolicies br- All Guests required to sign and return our Guest Occupancy Agreement. br- Minimum age of 30 years old to rent. br- Photo ID may be required upon check-inbr- Maximum car parking- 4- absolutely no street parkingbr- No smokingbr- NO Pets allowed br- Events, parties and large gatherings are strictly prohibited br- Additional fees and taxes may apply br- In lieu of a Refundable Damage Deposit, Aqua charges a non-refundable fee which provides up to $3000 of coverage towards unintentional rental property damages.br- Payments-50% down upon booking and final payment due 4 weeks prior to your arrival. May vary per listing site.brCANCELLATION POLICY: Policy may vary per booking channel. NO REFUNDS are given if the cancellation is received less than 30 days prior to the agreed upon arrival date. Agent will make reasonable efforts to rebook. All cancellations must be in writing and delivered to Agent by mail or email. There is no refund for early departure. br**Please note fees vary per booking site and some totals include the cleaning fee, damage waiver fee and booking fee others break out the fees. Some sites charge an additional booking fee.**

Bed

Bath

Sleeps

$277.14

/ Nightly

Private Vacation Home

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside, Michigan, United States

Carrie's Cottage is a duplex style cottage in Harbor Country that has two distinct sides perfect for group gatherings (both are included for the low nightly rate)! One side features three bedrooms, two full baths, full kitchen and MASSIVE great room ideal for hosting larger groups! The other side is a studio style set up with a third private full bathroom, and small kitchenette. The two units are separate and are both rented at booking unless otherwise requested. Each unit has it's own private entrance. The house has a large FENCED yard has mature trees, fire pit, and ample space to relax and hang out! brbrShort 5 min walk (less than 1/4 mile) to semi private beach (shared with 8 other homes) with TWO kayaks provided! We are located on a bluff so there are approximately 50 stairs down to the beach which may be diffucult for guests with health or joint issues. There is one rest bench along the way. Beach and bath towels NOT provided. No laundry facilities on site (laundromat about 1/2 mile away). Please note location of the property on map to Red Arrow Highway and train tracks. Train passes daily at approximately at 8a, 11a, 2p, and 8p. Pets must be crated whenever left unsupervised.

Bed

Bath

Sleeps

$1068.83

/ Nightly

Private Vacation Home

NEW! Warren Woods Pool Retreat on private 5 acres, new large heated pool & hotub

Lakeside, Michigan, United States

brSummer 2026 Calendar Open! Two weeks left (July 10-17) and (Aug 14 -21)!brbrbrEscape to Harbor County on this private 5-acre, and close to beaches, open concept 4 bedroom/3 bath updated home with large heated pool (16X36), outdoor hot tub, game room and two primary en-suite bedrooms! Have an electric vehicle You can charge your vehicle at our property with a universal charging station.brInterested in reviews We take pride in offering a great experience to our guests. See our reviews for Cherry Beach Pool House (Property ID 1881882).brWe want our guests to know we are committed to providing you a clean and safe vacation experience. Our cleaning service is following CDC recommendations for cleaning and maintenance.brThis ranch style home has an open floor plan with natural light filling the spacious living areas. Two Primary suites each with own private bathrooms. Additional queen bedroom and bunk room offer plenty of room for family and friends.brRelax in the three seasons room or step out onto large deck with lounge and dining areas, soak in the hot tub, fire up gas grill, or roast marshmallows in the firepit. With a 5-acre lot, you’ll have plenty of privacy and space to play. brProperty is adjacent to 108-acre wildlife preserve providing privacy and hiking trails.brThree-minute drive to Berrien Public Beach and five-minute drive to Cherry Beach.brbrThis home has many great features including:br• Drive or bike to great beaches. Quick three-minute drive to Berrien public beach or five-minute car ride to Cherry Beach, one of the largest and most sought-after beaches in the Harbor County area. br• Property adjacent to 108-acre wildlife preserve providing privacy and hiking trails. Trailhead one minute walk down Warren Woods Road. (Edward and Elizabeth Leonard Wildlife preserve: https://www.chikamingopenlands.org/our-preserves/the-edward-and-elizabeth-leonard-wildlife-preserve).brbr• NEW! Hot tub is open all season and is a ton of fun in the fall and winter months too.br• Attached garage converted into Game Room with Pop-A-Shot basketball, Foosball table and video games.br• Home sits on a private 5-acre lot, which offers lots of privacy, sun, and space to play.br• Outdoor fire pit.br• The entire home has been recently updated, with high end finishes throughout. br• This home is open concept and is large and comfortable for groups of 10 or more (set up to comfortably sleep 10).br• Fully equipped open concept kitchen with large island. br• We have plating for 12+ (i.e., dishes, silverware, glasses, etc.)br• Dining table is large and set for 8. Large island seats 4. Outdoor dining area seats 6.br• Comfortably sleeps 10. Two Primary suites each with king bed. Third bedroom with a queen bed and bunk room with two twin bunks (4 twin beds total)br• A pack and play, cot, highchair is also available. br• Large circular driveway offers plenty of parking (6+ cars)br• Minutes (drive) to Warren Dunes and many great breweries and wineries. br• There are also many excellent restaurants nearby. brbrThis is a great space for all seasons. Our extended family also enjoys this property frequently, so please contact me if you have any questions.

Bed

Bath

Sleeps

$580.56

/ Nightly

Private Vacation Home

Beach Lovers home w/Private Assoc Beach 1 blk fire pit scrnd porch

Lakeside, Michigan, United States

Please read before booking:br**Minimum age requirement of 30 years old br**Signed guest agreement requiredbr**Events, parties and large gatherings are strictly prohibited and could incur fines by local municipalities or removal from propertybrSaturday to Saturday rental during peak seasonbr3 nt minimum-Private Association Beach Access 1 block from housebrbrPlease be sure to check out all of Aqua Vacation Rentals 20+ properties located in Southwest Michigan! Our properties are listed on multiple booking sites and rates may vary. brPlease be sure to read all policies before booking.brbrAqua Vacation Rentals Lake Perch is a newly remodeled 2 bedroom, 1.5 bath home located in Lakeside just .1 miles from the private association beach. As you enter the home you immediately feel the stress release. The décor and location make this a perfect getaway to relax and unwind. The home is open and airy with lots of natural light. The screened porch is likely where you will spend much of your time enjoying coffee or a glass of wine. This home features a beautiful fireplace, AC/heat, internet, cable, gas grill, washer/dryer, a screened porch overlooking the backyard, a fire pit and much more. The private association beach is located just .1 mile from the house and is a wonderful spot to spend the day enjoy the water of Lake Michigan or watching a sunset in the evening. The grocery store, restaurants, wineries, breweries and Warren Dunes State Park are just a short drive away. brbrPolicies br- All Guests required to sign and return our Guest Occupancy Agreement. br- Minimum age of 30 years old to rent. br- Photo ID may be required upon check-inbr- Maximum car parking- 2- parking is at the back of the house in the circle drivebr- No smokingbr- NO Pets allowed br- Events, parties and large gatherings are strictly prohibited br- Additional fees and taxes may apply br- In lieu of a Refundable Damage Deposit, Aqua charges a non-refundable fee which provides up to $1500 of coverage towards unintentional rental property damages.br- Payments-50% down upon booking and final payment due 4 weeks prior to your arrival.brbrCANCELLATION POLICY: Policy may vary per booking channel. NO REFUNDS are given if the cancellation is received less than 30 days prior to the agreed upon arrival date. Agent will make reasonable efforts to rebook. All cancellations must be in writing and delivered to Agent by mail or email. There is no refund for early departure. br**Please note fees vary per booking site and some totals include the cleaning fee, damage waiver fee and booking fee others break out the fees. Some sites charge an additional booking fee.**

Bed

Bath

Sleeps

$989.39

/ Nightly

Private Vacation Home

LAKEFRONT HOME WITH PRIVATE HEATED POOL!

Lakeside, Michigan, United States

2 Bedrooms, 2 Baths, Sleeps 5brbrThree Night June Minimum!brbrPool OPEN until Sep 18th!brbrLake Breeze is located on Lake Michigan, with direct access to your private beach in your backyard! There is a very surprising amount of space in this two-bedroom charmer. You will love this very large and open kitchen, featuring an industrial stove, and brand new stainless fridge. Other common elements of the home are the large living room with fireplace and the adjacent sunroom. There is a nice dining area with ample seating, plus a couple of easy chairs to take advantage of the lake views. The master bedroom has the king bed, also on the Lake side, and the second bedroom has the full and a twin together. Additionally, there is a 12x40x3.5 foot deep lap pool (open Memorial Day-Sep 18th) and a lovely deck area. Located in Lakeside, on Lake Michigan.brbr**All Guests required to sign and return our Guest Occupancy Agreement.brbr**Minimum age of 25 years old to rent.brbr**Maximum two car parking.

Bed

Bath

Sleeps

$1146.23

/ Nightly

Private Vacation Home

Classic Cottage w Hot Tub, Steps from the Beach

Lakeside, Michigan, United States

Summary:brbrVacay Heaven, just a short walk from a stunning Lake Michigan beach! This spacious home, nestled on a lush, wooded 1/3-acre lot with an additional wooded back lot, offers privacy and R&R. It features a large living room with flat-screen TV, a fully-equipped kitchen, a fabulous 3-season porch, and 4 elegant bedrooms—one with an ensuite bath. Plus, enjoy a deluxe Jacuzzi, BBQ grill, fire pit, and 2 huge lawns for true bliss! Perfect for relaxation and fun with family and friends.brbrbrbrThe Space:brbrWhispering Arbor is a classic 1920s cottage where you’ll immediately feel your vacation spirit rising, thanks to the calm, relaxing atmosphere of the spacious, comfortably furnished home. The living room, with its lush natural lighting and great views, is graced by a wall of windows facing the landscaped front yard, expansive lawn, and tall, mature woods. Want to chill out with a favorite movie or show Grab a drink and plop down on the cozy couch or in a stylish barrel chair in front of the large flat-screen TV.brbrbrbrHungry for something scrumptious The recently updated kitchen features high-end appliances and all the utensils and essentials you’ll need to make delicious vacation meals or snacks. We’ve even seen to it that any coffee connoisseurs in your group can enjoy a cup of primo quality, Keurig-made coffee! In fact, the 4-seater dining table is a common gathering spot for a little morning joe and conversation about your vacay plans for the day.brbrbrbrThere’s also a sweet, nicely furnished 3-season screened porch, where you can relax with a glass of vino and get a closer connection to Mother Nature’s magnificent surrounding woods.brbrbrbrUpstairs, you’ll find a nice sitting room area, where you can curl up with a book to your heart’s content. And yes, this vacation rental is pet-friendly—just be sure to mention your pet when you make your reservation.brbrbrbrEach bedroom features plush, high-quality bedding and linens to ensure a sound sleep and sweet dreams, gorgeous natural lighting, plenty of storage space, and wonderful views of the surrounding woods.brbrbrbrMAIN FLOORbrbrPrimary Bedroom: 1 King bed with Ensuite bathroombrbrbrbr2ND FLOORbrbrBedroom 2: 1 Double BedbrbrBedroom 3: 1 King BedbrbrBedroom 4: 1 Queen BedbrbrbrbrAt Whispering Arbor, the bathrooms feature metro-style vanity sinks, tiled walk-in showers, and designer lighting and fixtures. There’s also a laundry room with a top-end washer and dryer combo—along with all the essentials—for your and your guests’ use.brbrbrbrOur guests know, firsthand, why they don’t call it The Great Outdoors for nothing. The surrounding property is professionally landscaped and rich with majestic tall trees. You’ll also find a set of comfy rattan chairs on the front porch and an inviting deluxe Jacuzzi where you and your guests can soothe yourselves after a long day of exploring. Or get a favorite beverage in hand and sit around the patio’s firepit in the evening, listening to birdsong as twilight turns to night and the stars magically appear in the sky. By the way, if a barbecued meal is desired, check out the fine gas grill on the patio—and chow down. Did we mention a long stretch of Lake Michigan’s fabulous, crystal-sand beach is just a short walk away Oh, yeah!brbrbrbrBesides being surrounded by natural beauty—and super-close to a premier beach—at Whispering Arbor, you can also enjoy the many fun activities afforded by being just a stone’s throw from the region’s largest recreational harbor, all sorts of woodland, lake, and riverside parks, acclaimed public golf courses, and hiking and biking trails galore. Plus, you’ll be close to excellent restaurants, art galleries, boutique shops, and popular watering holes in Lakeside, Union Pier, Three Oaks, and New Buffalo, as well as a host of nearby award-winning wineries and breweries.brbrbrbrOther Things to Note:brbrTo 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-24-0053

Bed

Bath

Sleeps

$249.89

/ Nightly

Private Vacation Home

UNION PIER HOME WITH PRIVATE HEATED POOL and BEACH ACCESS!

Lakeside, Michigan, United States

2 Bedrooms, 1 Bathroom, Sleeps 4brbrSummer Weeks Available!brbrPool OPEN May 23-October 01st!brbrCloud 9 sits comfortably on a large lot in Lakeside, directly next door to the path to the association beach access. When you first pull in the gates, you will notice the wonderful pool area and sizeable deck area. The cottage sits at the very edge of the property.brbrThe first things you will notice when you walk in the cottage are the soaring vaulted ceilings, and the gorgeous wood floors in the living area. The living room is beautifully appointed, with lots of great light. The bedrooms are smaller; one with a Queen, and one with two twins. There is one bathroom with a shower. Both the kitchen and dining areas are bright and cheery, with sliding glass doors leading to the outdoor deck area. Located in Lakeside, less than ½ block to the private beach.brbr**All Guests required to sign and return our Guest Occupancy Agreement.brbr**Minimum age of 25 years old to rent.

Bed

Bath

Sleeps

$487.49

/ Nightly

Private Vacation Home

Beautiful Lakeside MI vacation home with association beach access - late summer

Lakeside, Michigan, United States

*Beautifully decorated 3 bedroom, 2 bath, fully furnished cottage home*br*Newly updated kitchen, Bathroom and living room; with many historic features*br*Large, wooded lot has a swing set, multiple decks, birds singing often deer passing through*br*Bring firewood - firepit outside and Wood stove inside perfect for Winter, Spring and Fall*br*Separate beer and wine fridge to store your refreshments*br*Cottage comfortably sleeps 4 adults and four children or 6 adults: Queen (bedroom 1), Queen (bedroom 2), four twin (2 bunk beds), pull out couch*br*pack n play portable crib/ play yard available for babies/toddlers*br*Ideal for family vacations, girls wine and spa weekends, couples getaways*br*PRIVATE SHARED ASSOCIATION SANDY LAKE MICHIGAN BEACH ACCESS, approximately 1/2 mile walk; access to beach is ~50 stairs down*br*10 minute drive from New Buffalo downtown / city beach*br*10 minutes from Warren Dunes state park*br*Fire pit & gas grill in back yard*br* 3 seasons back Porch leading to large wood deck.br*Only 90 minutes from downtown Chicago; shorter drive from Chicago South Suburbs & NW IN*br*Enjoy awesome restaurants and establishments such as Red Arrow Roadhouse, Stray Dog, Redamak's, Beer Church Brewery, and Ghost Isle Brewery all within 10min drive*br*Close to wineries--perfect for girls weekends!!*br*10 minutes away from Four Winds Casino in New Buffalo and a quick 20 minute drive to Blue Chip Casino in Michigan City*br*Lighthouse Place Premium Outlets is the perfect spot to get good deal at all your favorite stores. Located in Michigan City!! Make sure to walk over to Shoreline Brewery and Restaurant in Michigan City after for a bite to eat and a drink*br*Farmers market only 2 minutes down red arrow highway (May - Oct)*brbr[Please note that beach conditions are variable, and we make no claims or promises about beach conditions in any area at any time. Listing photos are updated with recent pictures of the beach]brbr*Dogs are allowed on the beach but we do have restrictions. Dogs must be kept on a leash and are technically only allowed in the mornings and late afternoon/ evenings. The beach can get busier during the day in the summer so they don’t like dogs out during the daytime.

Bed

Bath

Sleeps

$1978.9

/ Nightly

Private Vacation Home

Blackwood Shores - 6 bed, pool, hot tub, game room

Lakeside, Michigan, United States

Experience luxury in this Harbor Country retreat with a heated pool, relaxing hot tub, and easy access to one of the area's best beaches. Lounge by the pool, enjoy sunset soaks and head to the beach for long walks and lakeside lounging. Inside, enjoy a gourmet kitchen with a large island, bright living spaces, a huge screened porch and a lively garage game room for ping pong and fun. Designed for connection, comfort, and relaxed lake living, this home delivers unforgettable vacation moments

Bed

Bath

Sleeps

$693.68

/ Nightly

Private Vacation Home

Private Assn Beach 500 FT Away, Fire Pit, Wooded

Lakeside, Michigan, United States

Escape to Sunset Breeze, a spacious Lakeside retreat with bright open living, a fully equipped kitchen, and room for the whole crew. Enjoy a king primary suite, two queen rooms, and a fun bunk room. Relax on the screened porch with a wood-burning fireplace or gather around the outdoor fire pit. Close to the lake and peaceful trails, it’s the perfect spot to unwind, reconnect, and savor Harbor Country living.

Bed

Bath

Sleeps

$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.

2

Bed

2

Bath

8

Sleeps

$731.38

/ Nightly

Private Vacation Home

Peaceful Family Getaway!

Lakeside, Michigan, United States

New construction build completed in Spring 24’ this (4) Bed, (3) full baths and (2) half baths sits on a .5 acre, partially wooded lot located on a private road in Lakeside ideal for family visits to enjoy a peaceful getaway. The home is located two blocks from the private beach on Lake Michigan (note there are roughly 85 steps down to private beach). Public beach access (no steps) 3 min drive. House sleeps 13 - three king beds, three twin and 1 full in bunk room. There is a pull out queen sofa bed in the upstairs den with TV. All bedrooms (except bunk room) have 55” TV’s. Large screened porch with 70” TV, weather-master window system and ceiling mounted heater for colder nights. Other amenities include upstairs laundry room, gas fire pit, synthetic turf bocce/putting/recreation court, 240V EV charger (tesla), (12) Beach chairs, Lily Pad, wagon, cooler, and beach toys. Two minute drive to Union Pier restaurants, bakery and grocery store; 10 minute drive to downtown New Buffalo. If you feel this sounds like the perfect getaway please come stay in this beautiful Lakeside gem!

Bed

Bath

Sleeps

$2155.41

/ Nightly

Private Vacation Home

Pool + Hot Tub | Fire Pit | Walk to Beach

Lakeside, Michigan, United States

Welcome to the Sycamore House! This stylish 4 bdrm 3.5 ba home is located in Harbor Country and just a 5 min walk to your private association beach on Lake Michigan.brbrEndless amenities abound at the Sycamore Housebr-two separate living rmsbr-heated in-ground pool/hot tubbr-outdoor showerbr-wood burning fire pit and gas fire pitbr-huge yard with trampolinebr-screened porch for gathering or diningbr-Peloton bike (bring your own shoes)br-No Pets, however owners have a dog so home is not `pet free`brbrPool is open Memorial Day Weekend through Columbus Day Weekend.brNo parties-no bachelor, no bachelorette, no prom partiesbrMust be at least 28yrs or older to bookbrMax number of guests strictly enforcedbrNo smoking, no petsbrQuiet hours strictly enforcedbrMax number of cars 5brbr*Our rules are strictly enforced and not adhering to them may result in us asking you to vacate the property immediately and a forfeiture of all monies paid.

Bed

Bath

Sleeps

$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

Bath

Sleeps

$492.36

/ Nightly

Private Vacation Home

Lakeside Home Close To Beach & Private Hot Tub! (3 Nt Min!)

Lakeside, Michigan, United States

2 Bedrooms, 1 Bath, Sleeps 04brbrThree Night Summer Minimum!brbrTucked Away in the sleepy town of Lakeside, we welcome you to Gus's Getaway! This two-bedroom, one bathroom home is just a short walk away from a gorgeous Lake Michigan association beach. Close to everything in Harbor Country too! Private back deck with outdoor hot tub (open year-round) perfect for soaking your worries away. Outdoor seating in both front and back of house. Gas grill waiting for your next great meal. brbrInterior of house is cute and cozy with lots of light throughout. Family room equipped with flat screen television. Warm up with the wood burning fireplace for those cool fall/winter evenings. Interior dining for four plus an adorable reading nook area. Fully stocked kitchen with island seating for two. Two bedrooms, one with a queen bed and one with a full. brbr All the amenities you would expect in a quality rental including hot tub, internet, cable, central heat/air, washer/dryer, gas grill, and more. brbr**All Guests required to sign and return our Guest Occupancy Agreement. brbr**Minimum age of 25 years old to rent. brbr**Maximum two car parking.

Bed

Bath

Sleeps

$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

3

Bed

2

Bath

8

Sleeps

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