Middlebury Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2 out of 5
Middlebury IN
$135 nightly
The price is $144 total per night
$144 total
Dec 14 - Dec 15
Total with taxes and fees
Located in Middlebury, this cottage is in a rural location, a 3-minute drive from Hunter Lake and 5 minutes from Corson Riverwoods County Park.
Kitchen
Free WiFi
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

Vandalia MI
$260 nightly
The price is $270 total per night
$270 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Located in Vandalia, this cottage is in a rural location, a 4-minute drive from Donnell Lake and 7 minutes from Paradise Lake.
Hot Tub
Kitchen
Spacious cottage by lake & walking trails, 1 mile from downtown Shipshe.

Spacious cottage by lake & walking trails, 1 mile from downtown Shipshe.

Shipshewana IN
Located in Shipshewana, this cottage is on a lake, within a 5-minute drive of Blue Gate Theater and Shipshewana Auction and Flea Market.
Kitchen
Washer
Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!

Howe IN
$224 nightly
The price is $258 total per night
$258 total
Dec 7 - Dec 8
Total with taxes and fees
Located in Howe, this cottage is on the waterfront, within a 15-minute drive of Parkview LaGrange Hospital and Oaklawn Terrace Park.
Kitchen
Free WiFi
The Wellington Cottage

The Wellington Cottage

3 out of 5
7420 N 1160 W Middlebury IN
$94 nightly
The price is $108 total per night
$108 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
With a stay at this cottage in Middlebury, you'll be on the waterfront, just steps from Stone Lake and a 2-minute drive from Fish Lake.
Parking included
Free WiFi
Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi

Elkhart IN
Located in Elkhart, this cottage is on the waterfront, within a 10-minute drive of Hall of Heroes Super Hero Museum and Wellfield Botanic Gardens.
Kitchen
Washer
Charming LaGrange 3-bedroom cottage less than 10 minutes from Shipshewana, IN!

Charming LaGrange 3-bedroom cottage less than 10 minutes from Shipshewana, IN!

LaGrange IN
$423 nightly
The price is $486 total per night
$486 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
When you stay at this cottage in LaGrange, you'll be within a 10-minute drive of Menno-Hof Museum of Culture and Blue Gate Performing Arts Center.
Kitchen
Washer
Carefree Lakefront Cottage/ 11 mins to skiing

Carefree Lakefront Cottage/ 11 mins to skiing

Jones MI
Located in Three Rivers, this cottage is on the waterfront, within a 15-minute drive of Corey Lake and Pleasant Lake.
Kitchen
Washer
Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm

Syracuse IN
$233 nightly
The price is $261 total per night
$261 total
Dec 28 - Dec 29
Total with taxes and fees
Located in Syracuse, this cottage is a 1-minute drive from Dewart Lake and 8 minutes from Tippecanoe Lake.
Hot Tub
Free WiFi
Cozy little lake cottage on Buck Lake!

Cozy little lake cottage on Buck Lake!

Vandalia MI
$294 nightly
The price is $294 total per night
$294 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Located in Vandalia, this cottage is on a lake, within a 10-minute drive of Donnell Lake and Paradise Lake.
Kitchen
Washer
Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan

2 out of 5
Sturgis MI
With a stay at this cottage in Sturgis, you'll be within a 15-minute drive of Lake Templene and Island Hills Golf Club.
Hot Tub
Kitchen
Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

Three Rivers MI
With a stay at this cottage in Three Rivers, you'll be within a 10-minute drive of Corey Lake and Pleasant Lake.
Hot Tub
Kitchen
Don't see what you're looking for?
See all available properties in Middlebury
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.

Middlebury Cottages essential information

Accommodation
82 Cottages
Lowest Price
$108
Highest Price
$486
Popular accommodation
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury, Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet, Spacious cottage by lake & walking trails, 1 mile from downtown Shipshe., Live & Love Life on the Lake at Sunset Cottage!, The Wellington Cottage, Charming 2-bedroom cottage "on Simonton Lake" in delightful Elkhart with WiFi, Charming LaGrange 3-bedroom cottage less than 10 minutes from Shipshewana, IN!, Carefree Lakefront Cottage/ 11 mins to skiing, Cozy lake Cottage on Dewart Lake with hottub, 1 mile from Blue Barn Berry Farm, Cozy little lake cottage on Buck Lake! , Cozy, Relaxing, Romantic, Fun All Sports Lake Cottage in Southwest Michigan, Cozy lakeside home in Three Rivers, great for an outdoorsy bunch!

Explore more Cottages

Types of Hotels

Top 20 Middlebury Hotels

Hotels Near Middlebury

Top Hotel Brands

Hotels By Star Rating

Cities near Middlebury