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A sunset over a body of water with two tents on a grassy field.

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    Check prices for these dates

    Check prices for these dates, 15 – 16 December 2026

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    Our top choices for Lakeside cottages

    1. Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!

    A gravel path leading to a small house with a white porch and a fenced yard.

    2. 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach

    Ceiling fans keep air flow and also Central Air and Heat.

    3. Private Beach Steps to the Lake.

    A wooden deck with a bench and two chairs, overlooking a body of water and trees.

    4. Treehouse Bungalow- Quaint and Cozy Getaway!

    A covered outdoor seating area with a sofa, two chairs, and a coffee table.

    5. Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!

    A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

    6. 8-acre Bridgman Oasis: Pool, Hot Tub & Game Room

    A two-story house with a large backyard, a fire pit, and outdoor seating.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Lakeside

    This charming Lake Michigan beach town offers antique shops and art galleries along its quaint Red Arrow Highway. Spend summer days at the pristine Lakeside beaches, then grab homemade ice cream at local shops before exploring nearby Warren Dunes State Park.

    See all hotels in Lakeside

    A sunset over a body of water with two tents on a grassy field.

    Top reviews in Lakeside

    Four Winds Casino Resort – New Buffalo

    A multi-story hotel with a symmetrical facade, large windows, and a central entrance.

    The Brewery Lodge Hotel

    A two-story brick house with a gabled roof, surrounded by a well-maintained garden with various plants and a lawn.

    Tru by Hilton Saint Joseph

    A modern building with a 'Now Open' sign, featuring a central entrance with a yellow canopy, multiple windows, and a parking lot with cars.

    Quality Inn Sawyer

    A multi-story hotel with a covered entrance and a parking lot.

    The Blue Heron Inn

    A building with a sign reading "The Blue Heron Inn" and a blue awning labeled "Lobby".

    Comfort Inn La Porte

    A Comfort Inn hotel with a covered entrance, multiple floors, and a parking lot.

    Holiday Inn Express & Suites Michigan City by IHG

    A Holiday Inn Express & Suites building with a covered entrance, multiple floors, and a parking lot.

    Fairfield Inn & Suites by Marriott St. Joseph Stevensville

    A Fairfield Inn & Suites Marriott hotel entrance with a stone facade, large windows, and a curved overhang.

    Frequently Asked Questions

    How much do cottages in Lakeside cost?

    Expect to pay between £157 and £856 per night for cottages in Lakeside. Whatever your budget, a wonderful stay is just a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

    What are the best cottages in Lakeside?

    Pick from multiple cottages in Lakeside with a total average guest review rating of 9.6. Fire Fly Resort is a comfortable place to put your feet up between adventures. This 3.5-star cottage also features a garden and individually decorated rooms. Union Pier - Alex 2 Bedroom Cottage is another quality option with visitors in this area. It has a 3-star rating and amenities including a barbecue grill and WiFi.

    How many cottages are there in Lakeside?

    Get in touch with nature in one of the cottages on offer in Lakeside. To help you reserve your ideal stay, use our filter tool to search for perks or amenities you need.

    Are there any family-friendly cottages in Lakeside?

    Travelling with the family in Lakeside is a cinch at Fire Fly Resort. With conveniences including a picnic area and a barbecue grill, you'll find all the comforts you need at this 3.5-star cottage. Union Pier - Alex 2 Bedroom Cottage is another family-friendly pick where everyone can escape the frantic pace of big city life. This cottage has a 3-star rating and conveniences including WiFi and a barbecue grill. Once you've checked in, there's no shortage of family-friendly attractions to discover around Lakeside. Whittaker Woods Golf Course and Warren Dunes State Park guarantee a good time for young and old.

    Why book your cottage in Lakeside with Expedia?

    Expedia has some wonderful cottages in Lakeside, so start planning for a memorable holiday on nature's doorstep. If you have a fixed budget, click on how much you're willing to spend and the star rating of your property. Or, make the most of our filters to search for cottages with a hot tub or a kitchen. We'll help you find the perfect place whatever your bank balance or plans.

    How can I find cheap cottages in Lakeside?

    A great way to spot cheap cottages in Lakeside is with Expedia's convenient filter tool. Narrow your search by star rating, budget and amenities to take advantage of unbeatable deals with only a few clicks.

    What is there to do in Lakeside near my cottage?

    The most practical travel accessory is a well-planned itinerary. Burnison Galleries is a good place to start your adventures in Lakeside.