Compare Chesterton Cottage Rentals

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Featured Cottages in Chesterton

Simple Cottage Set in the Woods by Lake Michigan

Simple Cottage Set in the Woods by Lake Michigan

New Buffalo MI
At this cottage, guests have access to features like laundry facilities. This golf cottage also has barbecue grills.
Kitchen
Washer
Cozy pet-friendly cottage near Lake Michigan

Cozy pet-friendly cottage near Lake Michigan

Grand Beach MI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*

Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*

Michigan City IN
At this cottage, guests have access to features like laundry facilities. This family-friendly cottage also has barbecue grills.
Kitchen
Washer
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

New Buffalo MI
$469 nightly
The price is $483 total per night
$483 total
Nov 8 - Nov 9
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
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 IN
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Spacious 3BR House With Firepit & Grill, Near Beach

Spacious 3BR House With Firepit & Grill, Near Beach

2 out of 5
North Hamilton Street 234 Gary IN
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

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

New Buffalo MI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Private Beach Steps to the Lake.

Private Beach Steps to the Lake.

Union Pier MI
$1,096 nightly
The price is $1,096 total per night
$1,096 total
Nov 8 - Nov 9
Total with taxes and fees
Guests of this cottage enjoy access to a private beach, laundry facilities, and a garden. This beach cottage also has barbecue grills.
Kitchen
Washer
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

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

Gary IN
At this cottage, guests have access to laundry facilities, local meal delivery service, and barbecue grills. This family-friendly cottage also has a garden.
Kitchen
Washer
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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
    $95 nightly
    The price is $107 total per night from Nov 8 to Nov 9
    $107 total
    Nov 8 - Nov 9
    Total with taxes and fees
    8.8/10 Excellent! (1,005 reviews)
    Best Western Indian Oak

    Best Western Indian Oak

    558 Indian Boundary Road Chesterton IN
    $89 nightly
    The price is $100 total per night from Nov 16 to Nov 17
    $100 total
    Nov 16 - Nov 17
    Total with taxes and fees
    Fairbridge Inn Express Chesterton

    Fairbridge Inn Express Chesterton

    713 Plaza Dr. Chesterton IN
    $78 nightly
    The price is $88 total per night from Dec 6 to Dec 7
    $88 total
    Dec 6 - Dec 7
    Total with taxes and fees
    6.8/10 (397 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
92 Cottages
Lowest Price
$88
Highest Price
$1,096
Popular accommodation
Simple Cottage Set in the Woods by Lake Michigan, Cozy pet-friendly cottage near Lake Michigan, Walk to Lake Michigan Beach from Cottage in the Woods - *Seaside Fired Smores*, 3BR 2b New Buff cottage dogs ok, steps to dwntn restaurants&shops, walk to beach, Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk, Spacious 3BR House With Firepit & Grill, Near Beach, Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5, Private Beach Steps to the Lake., Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

More to Explore