Compare Middlebury Cottage Rentals

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Featured Middlebury Cottages

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
Nov 30 - Dec 1
Total with taxes and fees
At this cottage, guests have access to a garden.
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
$220 nightly
The price is $228 total per night
$228 total
Dec 1 - Dec 2
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
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
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!

Howe IN
$218 nightly
The price is $251 total per night
$251 total
Nov 25 - Nov 26
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
The Wellington Cottage

The Wellington Cottage

3 out of 5
7420 N 1160 W Middlebury IN
$60 nightly
The price is $69 total per night
$69 total
Dec 7 - Dec 8
Total with taxes and fees
Renovated in 2018, this cottage offers free WiFi in public areas, a 24-hour business center, and a computer station. You can take advantage of free parking if you drive. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Other amenities at this family-friendly cottage include a library, laundry facilities, and barbecue grills.
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
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
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
Nov 30 - Dec 1
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Carefree Lakefront Cottage/ 11 mins to skiing

Carefree Lakefront Cottage/ 11 mins to skiing

Jones MI
At this cottage, guests have access to an arcade/game room, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
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
$296 nightly
The price is $332 total per night
$332 total
Nov 25 - Nov 26
Total with taxes and fees
This cottage features a hot tub and barbecue grills.
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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 Middlebury

    Hampton Inn & Suites Middlebury

    Hampton Inn & Suites Middlebury

    105 Crystal Heights Blvd Middlebury IN
    $111 nightly
    The price is $125 total per night from Dec 1 to Dec 2
    $125 total
    Dec 1 - Dec 2
    Total with taxes and fees
    8.2/10 Very Good! (1,001 reviews)
    Essenhaus Inn & Conference Center

    Essenhaus Inn & Conference Center

    240 Hwy 20 Middlebury IN
    $109 nightly
    The price is $122 total per night from Nov 30 to Dec 1
    $122 total
    Nov 30 - Dec 1
    Total with taxes and fees
    9.6/10 Exceptional! (1,009 reviews)
    Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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

    Middlebury IN
    $135 nightly
    The price is $144 total per night from Nov 30 to Dec 1
    $144 total
    Nov 30 - Dec 1
    Total with taxes and fees
    9.8/10 Exceptional! (40 reviews)

Cottages

Book a cottage in Middlebury
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Middlebury. 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 Middlebury better.

Cottage apartments in Middlebury 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 Middlebury
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 Middlebury 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 Middlebury 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 Middlebury. 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.

Middlebury Cottages essential information

Accommodation
95 Cottages
Lowest Price
$69
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