Compare Chesterton Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Chesterton Cottages

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. Other amenities at this family-friendly cottage include a garden and a water dispenser.
Beachglass Cottage - Family Friendly Kids and Pets

Beachglass Cottage - Family Friendly Kids and Pets

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

At this cottage, guests have access to laundry facilities, local meal delivery service, and barbecue grills. This family-friendly cottage also has a garden.
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration

Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration

Guests staying at this cottage enjoy a water park, a hot tub, and laundry facilities. This smoke-free cottage also has barbecue grills.
Treehouse Bungalow- Quaint and Cozy Getaway!

Treehouse Bungalow- Quaint and Cozy Getaway!

$425 nightly
The price is $476 total per night
$476 total
Aug 4 - Aug 5
Total includes taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries

Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
The Hideaway House - Private, Peaceful, Cozy

The Hideaway House - Private, Peaceful, Cozy

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Cozy Michigan City Cottage #1

Cozy Michigan City Cottage #1

At this cottage, guests have access to barbecue grills.
Don't see what you're looking for?
See all available properties in Chesterton
View all properties
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.

Hotel Options in Chesterton

    Spring House Inn

    Spring House Inn

    303 N Mineral Springs Rd, Chesterton, IN
    $129 nightly
    The price is $144 total per night from Aug 3 to Aug 4
    $144 total
    Aug 3 - Aug 4
    Total includes taxes and fees
    8.8/10 Excellent! (1,006 reviews)
    Best Western Indian Oak

    Best Western Indian Oak

    558 Indian Boundary Road, Chesterton, IN
    $130 nightly
    The price is $146 total per night from Aug 10 to Aug 11
    $146 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    8.4/10 Very Good! (1,004 reviews)
    Waterbird Lakeside Inn

    Waterbird Lakeside Inn

    556 Indian Boundary Road, Chesterton, IN
    $112 nightly
    The price is $125 total per night from Jul 13 to Jul 14
    $125 total
    Jul 13 - Jul 14
    Total includes taxes and fees
    8/10 Very Good! (870 reviews)

Cottages

Book a cottage in Chesterton
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chesterton. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chesterton better.

Cottage apartments in Chesterton range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chesterton
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chesterton and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chesterton cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chesterton. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chesterton Cottages essential information

Accommodation
102 Cottages
Lowest Price
$125
Highest Price
$476
Popular accommodation
Cozy New Buffalo cottage with hot tub & fire pit. Short walk to downtown!, Beachglass Cottage - Family Friendly Kids and Pets, Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park , Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5, Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration, Treehouse Bungalow- Quaint and Cozy Getaway! , Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries, The Hideaway House - Private, Peaceful, Cozy, Cozy Michigan City Cottage #1

Cottages in Chesterton

Most Popular

More Places To Stay in Chesterton

Book on Expedia