A calm river with a bridge, surrounded by autumn-colored trees and a dock with boats.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Lakeside cottages

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

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

Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
Three Oaks
9.4 out of 10, Exceptional, (82 reviews)
"Great to walk to town. Nice area to road bike etc."
United States
jeffrey
The price is £216
includes taxes & fees
12 Oct - 13 Oct
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!
Quintessential lake cottage

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

3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
Downtown New Buffalo
10.0 out of 10, Exceptional, (18 reviews)
"Great property with excellent location to all downtown activities as well as the beach."
United States
christian s.
The price is £352
includes taxes & fees
7 Oct - 8 Oct
3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach
A covered outdoor seating area with a sofa, two chairs, and a coffee table.

3. Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!
Michigan City
8.6 out of 10, Excellent, (60 reviews)
"Very cute and comfortable. "
United States
Jacqueline C.
The price is £251
includes taxes & fees
5 Oct - 6 Oct
Treehouse Bungalow- Quaint and Cozy Getaway!
A wooden deck with a black sofa, a table with a plant, and a pergola with lights.

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

Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
New Buffalo
10.0 out of 10, Exceptional, (26 reviews)
"Perfect stay! The house was spotless, stylish, and located perfectly. Tori was incredibly responsive. Highly recommended"
United States
kimberly b.
The price is £510
includes taxes & fees
27 Oct - 28 Oct
Secluded Retreat, Hot Tub, Fire Pit, Wildlife Views, Near New Buffalo Beach!
A wooden deck with a bench and two chairs, overlooking a body of water and trees.

5. Private Beach Steps to the Lake.

Private Beach Steps to the Lake.
Union Pier
10.0 out of 10, Exceptional, (97 reviews)
"Great stay for a week by the beach with family! Perfect location to walk right down to the beach each day. Excited to come back one day!"
United States
Jalen W.
The price is £835
includes taxes & fees
12 Oct - 13 Oct
Private Beach Steps to the Lake.
A two-story building with a balcony, a front door, and a sign that reads 'Sweet Inn.'

6. Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk

Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Michigan City
9.6 out of 10, Exceptional, (59 reviews)
"Great space, fun neighborhood, and perfect location."
United States
Eric B.
The price is £408
includes taxes & fees
1 Oct - 2 Oct
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
A small, dark wooden cabin with a porch and steps, surrounded by grass and trees.

7. Perfect getaway! Modern, rustic cottage on the St. Joseph River.

Perfect getaway! Modern, rustic cottage on the St. Joseph River.
St. Joseph
9.8 out of 10, Exceptional, (14 reviews)
"Julie was very responsive via messages as my parents were staying here and I was the main contact. They enjoyed their stay very much! "
United States
Raymie G.
The price is £304
includes taxes & fees
1 Oct - 2 Oct
Perfect getaway! Modern, rustic cottage on the St. Joseph River.
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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Top Lakeside Hotel Reviews

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

10/10 Excellent
"We enjoyed our stay. The staff was so friendly. Room was very clean and quiet."
Donna 1-night trip
Posted 1 hour ago
Four Winds Casino Resort – New Buffalo

Find out more about Lakeside

Lakeside Cottages information

Number of reviews
219
Accommodation
166 Cottages
Lowest Price
£216
Highest Price
£835

Frequently asked questions

How much do cottages in Lakeside cost?
Expect to pay between £216 and £835 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 9.8. 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 166 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.