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Photo by Indiana Office of Tourism Development
Open Photo by Indiana Office of Tourism Development
Chesterton long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Chesterton
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:2 Feb - 2 Mar
Image gallery for VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
9.09.0 out of 10, Wonderful, (22 reviews)
Wonderful
(22 reviews)
VIP! LUXURY 4BD 5min to Lake Michigan beach Big Pool with heater!!
Michigan City, IN
16% off
Price is AU$8,162
AU$8,162
for 28 nights, 1 villa
AU$291 per night
includes taxes & fees
Image gallery for Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
1010 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Gary, IN
12% off
Price is AU$4,917
AU$4,917
for 28 nights, 1 cottage
AU$176 per night
includes taxes & fees
Image gallery for Charming Miller Beach Cottage
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Charming Miller Beach Cottage
Gary, IN
12% off
Price is AU$8,912
AU$8,912
for 28 nights, 1 home
AU$318 per night
includes taxes & fees
Image gallery for Dunes Homestead - Near Dunes + Lake + Dog Friendly
9.89.8 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Dunes Homestead - Near Dunes + Lake + Dog Friendly
Chesterton, IN
17% off
Price is AU$7,204
AU$7,204
for 28 nights, 1 home
AU$257 per night
includes taxes & fees
Image gallery for Cozy and Charming Beach Getaway on Lovely Lake Michigan
9.89.8 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)
Cozy and Charming Beach Getaway on Lovely Lake Michigan
Chesterton, IN
8% off
Price is AU$9,266
AU$9,266
for 28 nights, 1 cottage
AU$331 per night
includes taxes & fees
Image gallery for The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Chesterton, IN
8% off
Price is AU$6,607
AU$6,607
for 28 nights, 1 home
AU$236 per night
includes taxes & fees
Image gallery for The 8th Street ART House. Relax and be inspired!
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
The 8th Street ART House. Relax and be inspired!
Michigan City, IN
15% off
Price is AU$8,578
AU$8,578
for 28 nights, 1 home
AU$306 per night
includes taxes & fees
Image gallery for Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
1010 out of 10, Exceptional, (136 reviews)
Exceptional
(136 reviews)
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Lakeside, MI
9% off
Price is AU$10,693
AU$10,693
for 28 nights, 1 cottage
AU$382 per night
includes taxes & fees
Image gallery for The Getaway - Three Oaks Cottage 3 BR 1.5 Bath - Week Stay Discount
1010 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
The Getaway - Three Oaks Cottage 3 BR 1.5 Bath - Week Stay Discount
Three Oaks, MI
41% off
Price is AU$6,733
AU$6,733
for 28 nights, 1 home
AU$240 per night
includes taxes & fees
Image gallery for Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
1010 out of 10, Exceptional, (116 reviews)
Exceptional
(116 reviews)
Modern Farmhouse Retreat-10 Min Walk to Lake Michigan-Hot Tub-Sauna
Michigan City, IN
8% off
Price is AU$18,360
AU$18,360
for 28 nights, 1 home
AU$656 per night
includes taxes & fees
Image gallery for 1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
9.29.2 out of 10, Wonderful, (66 reviews)
Wonderful
(66 reviews)
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside, MI
9% off
Price is AU$8,349
AU$8,349
for 28 nights, 1 cottage
AU$298 per night
includes taxes & fees
Image gallery for Lake Michigan, Indiana Beachfront Vacation Rental
1010 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)
Lake Michigan, Indiana Beachfront Vacation Rental
Chesterton, IN
25% off
Price is AU$11,741
AU$11,741
for 28 nights, 1 cottage
AU$419 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house with WiFi, AC in lovely Michigan City
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Charming 2-bedroom house with WiFi, AC in lovely Michigan City
Michigan City, IN
17% off
Price is AU$4,690
AU$4,690
for 28 nights, 1 home
AU$168 per night
includes taxes & fees
Image gallery for Lake Shore Beach House. Across The Alley From Our Stunning Beach
1010 out of 10, Exceptional, (107 reviews)
Exceptional
(107 reviews)
Lake Shore Beach House. Across The Alley From Our Stunning Beach
Gary, IN
16% off
Price is AU$10,384
AU$10,384
for 28 nights, 1 home
AU$371 per night
includes taxes & fees
Image gallery for Beautiful Private Cottage, Sleeps 6, Walk to Beach
1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
Beautiful Private Cottage, Sleeps 6, Walk to Beach
New Buffalo, MI
9% off
Price is AU$14,638
AU$14,638
for 28 nights, 1 cottage
AU$523 per night
includes taxes & fees
Image gallery for Indiana Dunes 2-Bedroom Beach Rental
9.89.8 out of 10, Exceptional, (55 reviews)
Exceptional
(55 reviews)
Indiana Dunes 2-Bedroom Beach Rental
Chesterton, IN
8% off
Price is AU$13,906
AU$13,906
for 28 nights, 1 cottage
AU$497 per night
includes taxes & fees
Image gallery for Charming Beach Front Cottages at Duneland Rentals.
1010 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
Charming Beach Front Cottages at Duneland Rentals.
Chesterton, IN
8% off
Price is AU$13,985
AU$13,985
for 28 nights, 1 cottage
AU$499 per night
includes taxes & fees
Image gallery for National Park Nature Retreat access to train to Chicago and 2 close to Beach
9.69.6 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
National Park Nature Retreat access to train to Chicago and 2 close to Beach
Michigan City, IN
35% off
Price is AU$12,533
AU$12,533
for 28 nights, 1 home
AU$448 per night
includes taxes & fees
Image gallery for Cozy cute home recently rehabbed with 5 min to outlet mall, casino
9.69.6 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Cozy cute home recently rehabbed with 5 min to outlet mall, casino
Michigan City, IN
12% off
Price is AU$5,410
AU$5,410
for 28 nights, 1 home
AU$193 per night
includes taxes & fees
Image gallery for Remodeled, Washer, Dryer, Mins to Beach & Downtown
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Remodeled, Washer, Dryer, Mins to Beach & Downtown
Michigan City, IN
8% off
Price is AU$5,496
AU$5,496
for 28 nights, 1 apartment
AU$196 per night
includes taxes & fees
Image gallery for 'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
1010 out of 10, Exceptional, (137 reviews)
Exceptional
(137 reviews)
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
New Buffalo, MI
9% off
Price is AU$8,527
AU$8,527
for 28 nights, 1 apartment
AU$305 per night
includes taxes & fees
Image gallery for No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
No Cleaning Fee! Cozy Cottage in Dunes National Park, Beverly Shores Indiana.
Michigan City, IN
8% off
Price is AU$7,547
AU$7,547
for 28 nights, 1 home
AU$270 per night
includes taxes & fees
Image gallery for Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park
9.69.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park
Chesterton, IN
15% off
Price is AU$11,825
AU$11,825
for 28 nights, 1 home
AU$422 per night
includes taxes & fees
Image gallery for That 70’s Loft- Peace, Love and a Funky Stay!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
That 70’s Loft- Peace, Love and a Funky Stay!
Chesterton, IN
8% off
Price is AU$9,230
AU$9,230
for 28 nights, 1 apartment
AU$330 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value