Cottage
10.0(68 Reviews)
2 Bedrooms
6 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $177/Night
7 Nights - US $1,236
Middlebury Summer Rentals, Cottages & Cabins
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Compare Summer Rental in Middlebury
10.0
House
9.1(16 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Air Conditioner
Internet
US $162/Night
7 Nights - US $1,131
Cottage
10.0(10 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $131/Night
7 Nights - US $918
House
10.0(1 Review)
1 Bedroom
2 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $239/Night
7 Nights - US $1,674
US $159/Night
7 Nights - US $1,113
House
1 Bedroom
- Internet
Child Friendly
Barbecue/Outdoor Cooking
Sports/Activities
US $534/Night
7 Nights - US $3,741
House
9.6(30 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $184/Night
7 Nights - US $1,285
US $167/Night
7 Nights - US $1,168
Cabin
10.0(39 Reviews)
3 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $546/Night
7 Nights - US $3,820
US $128/Night
7 Nights - US $894
House
10.0(32 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $326/Night
7 Nights - US $2,284
House
10.0(11 Reviews)
3 Bedrooms
9 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $324/Night
7 Nights - US $2,267
House
9.6(24 Reviews)
3 Bedrooms
9 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $287/Night
7 Nights - US $2,011
House
6 Bedrooms
23 Guests
Private Pool- Parking
Pool- Balcony/Terrace
US $1,061/Night
7 Nights - US $7,430
House
10.0(27 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $206/Night
7 Nights - US $1,442
House
8.0(5 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $259/Night
7 Nights - US $1,813
About Middlebury Summer Rental on Casai.com
With 16 summer rental in or near Middlebury? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.
Our holiday homes and villas in Middlebury come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.
Searching for a relaxing retreat in Middlebury to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Middlebury.
Summer Rental: Explore Top Destinations
Frequently Asked Questions About Middlebury Luxury Rentals
How many summer rentals are available around Middlebury, IN?
In 2026, Casai offers 16 summer rentals in or around Middlebury. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
How much does it cost to rent a summer rental in Middlebury?
The average price per night for a summer rental in Middlebury is $306. Check the full list of summer accommodations in Middlebury.
How many summer rentals are available to book in Middlebury?
There are 16 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.com.
Do any summer rentals in Middlebury have a private pool?
Yes, here are some popular summer holiday rentals in Middlebury that have a private or indoor pool:
- Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
- Lakin' It Easy
- The Wellington Cottage
- Modern Amish Country Tiny Home with Outdoor Shower
Check all holiday rentals with a pool in Middlebury on Casai.com.
Can I rent pet-friendly summer rentals in Middlebury?
Yes, We have 16 summer rental homes in Middlebury and types of place to stay in Middlebury include:
- Vacation Homes: 16 available for rent
- Villas: 16 Rentals available for rent
- Holiday Apartments: 16 Rentals available for rent
- Hotels with Suites: 16 Rentals available for book
Do you have a luxury summer rental with a pool in Middlebury?
Yes, of course! There are many luxury summer rental properties in Middlebury. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Middlebury.
