129+ Private Villas and Holiday Rentals in Middlebury |
Middlebury Holiday Rentals
Apartment
- Torrington
- ·
- Watertown
- 1.12 mi to center
10.0Exceptional
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
495 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $103/Night
7 Nights - US $719
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
850.35 ft²
- Fireplace/Heating
View
Pet Friendly- Parking
US $203/Night
7 Nights - US $1,419
House
1 Bedroom
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
US $1,629/Night
7 Nights - US $11,400
Cottage
- Torrington
- ·
- Watertown
- 2.39 mi to center
9.4Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $219/Night
7 Nights - US $1,530
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
7104.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
US $101/Night
7 Nights - US $709
Cottage
- Torrington
- ·
- Watertown
- 0.69 mi to center
9.2Exceptional
(42 Reviews)
2 Bedrooms
1 Bath
6 Guests
889 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $258/Night
7 Nights - US $1,807
Apartment
- Torrington
- ·
- Watertown
- 0.41 mi to center
9.2Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $346/Night
7 Nights - US $2,422
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
Internet
US $137/Night
7 Nights - US $957
House
10.0Exceptional
(164 Reviews)
4 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $244/Night
7 Nights - US $1,711
Luxury Holiday Rentals in Middlebury
Over 120+ Luxury Holiday Rentals in or Near Middlebury
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,723/Night
7 Nights - US $12,062
House
7 Bedrooms
5 Baths
12 Guests
- Air Conditioner
- Internet
Child Friendly
Wheelchair Accessible
US $1,168/Night
7 Nights - US $8,176
Hotel
4 Baths
Hot Tub
Spa- Fireplace/Heating
- Pool
US $977/Night
7 Nights - US $6,842
Hotel
4 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $977/Night
7 Nights - US $6,842
House
- Torrington
- ·
- Watertown
- 1.08 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $809/Night
7 Nights - US $5,660
House
4 Bedrooms
3 Baths
10 Guests
3326.05 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Pool
US $804/Night
7 Nights - US $5,626
House
7.6Very Good
(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
3321 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $797/Night
7 Nights - US $5,577
Hotel
3 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $733/Night
7 Nights - US $5,128
Hotel
3 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $733/Night
7 Nights - US $5,128
Top-Rated Holiday Rentals with a Pool in Middlebury
Over 24+ The Best Private Villas and Holiday Rentals in Middlebury with a Pool
House
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $173/Night
7 Nights - US $1,211
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $182/Night
7 Nights - US $1,275
Hotel
8.5Fabulous
(412 Reviews)
5 Baths
279.86 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $230/Night
7 Nights - US $1,607
Hotel
8.4Excellent
(1005 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $171/Night
7 Nights - US $1,198
Hotel
8.2Excellent
(1199 Reviews)
1 Bath
- Pool
Breakfast- Kitchen
- Parking
US $109/Night
7 Nights - US $766
Hotel
8.0Excellent
(689 Reviews)
12 Baths
99.57 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
US $151/Night
7 Nights - US $1,055
Hotel
7.9Very Good
(270 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $185/Night
7 Nights - US $1,293
House
3 Bedrooms
3 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $632/Night
7 Nights - US $4,423
Hotel
2 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $489/Night
7 Nights - US $3,421
Pet-Friendly Holiday Rentals in Middlebury
Over 26+ Pet-Friendly Holiday Rentals in or Near Middlebury
House
10.0Exceptional
(53 Reviews)
4 Bedrooms
2 Baths
8 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $389/Night
7 Nights - US $2,720
House
- Connecticut
- ·
- Oakville
- 0.42 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1905.21 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $323/Night
7 Nights - US $2,259
Cottage
- Connecticut
- ·
- Oakville
- 0.31 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $538/Night
7 Nights - US $3,769
House
- Connecticut
- ·
- Oakville
- 0.42 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $310/Night
7 Nights - US $2,173
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
807.29 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $187/Night
7 Nights - US $1,307
New
House
- Torrington
- ·
- Watertown
- 0.68 mi to center
3 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $216/Night
7 Nights - US $1,511
Cottage
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $226/Night
7 Nights - US $1,583
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $233/Night
7 Nights - US $1,629
Apartment
9.6Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
1020 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $278/Night
7 Nights - US $1,949
Large Holiday Rentals and Private Villas in Middlebury
Over 13+ Large Holiday Rentals and Private Villas in or Near Middlebury
House
9.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
10 Guests
1700 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Internet
US $254/Night
7 Nights - US $1,777
House
5.5Average
(52 Reviews)
5 Bedrooms
9 Baths
12 Guests
161.46 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $58/Night
7 Nights - US $406
House
9.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,395/Night
7 Nights - US $9,765
House
3.7Average
(54 Reviews)
6 Bedrooms
6 Baths
8 Guests
1471.07 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $58/Night
7 Nights - US $406
House
- Torrington
- ·
- Watertown
- 1.26 mi to center
6 Bedrooms
5 Baths
19 Guests
5800 ft²
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $1,336/Night
7 Nights - US $9,351
House
10.0Exceptional
(1 Review)
6 Bedrooms
5 Baths
12 Guests
3500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,057/Night
7 Nights - US $7,398
House
9.0Exceptional
(4 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $851/Night
7 Nights - US $5,954
Apartment
7.8Very Good
(18 Reviews)
3 Bedrooms
2 Baths
10 Guests
1000 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $157/Night
7 Nights - US $1,099
House
- New Haven
- ·
- Middlebury
- 1.72 mi to center
5.0Average
(2 Reviews)
6 Bedrooms
5 Baths
18 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,718/Night
7 Nights - US $12,026
Wheelchair Accessible Holiday Homes in Middlebury
Over 12+ Wheelchair Accessible Holiday Homes in or Near Middlebury
Hotel
2 Baths
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $489/Night
7 Nights - US $3,421
Hotel
8.4Excellent
(726 Reviews)
2 Baths
355.21 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $139/Night
7 Nights - US $973
Hotel
8.4Excellent
(1223 Reviews)
1 Bath
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $114/Night
7 Nights - US $797
Hotel
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $245/Night
7 Nights - US $1,715
Hotel
7.5Very Good
(221 Reviews)
1 Bath
204.51 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $331/Night
7 Nights - US $2,317
Hotel
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $245/Night
7 Nights - US $1,715
Hotel
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $225/Night
7 Nights - US $1,577
Hotel
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $225/Night
7 Nights - US $1,577
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
US $83/Night
7 Nights - US $578
Middlebury Private Villas and Holiday Homes Under $200
Over 39+ Middlebury Private Villas and Holiday Homes Under $200
Apartment
- Torrington
- ·
- Watertown
- 2.89 mi to center
8.6Fabulous
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $115/Night
7 Nights - US $805
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
172.22 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $104/Night
7 Nights - US $725
Hotel
8.0Excellent
(1010 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $109/Night
7 Nights - US $761
Apartment
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
4 Guests
660 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $132/Night
7 Nights - US $921
Apartment
- Torrington
- ·
- Watertown
- 2.73 mi to center
9.1Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
376.74 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $96/Night
7 Nights - US $672
Apartment
- New Haven
- ·
- Middlebury
- 1.22 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $130/Night
7 Nights - US $907
House
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $131/Night
7 Nights - US $918
Apartment
1 Bedroom
1 Bath
2 Guests
2400 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $177/Night
7 Nights - US $1,238
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $151/Night
7 Nights - US $1,060
Instantly Bookable Holiday Homes in Middlebury
Over 21+ Instantly Bookable Holiday Homes in or Near Middlebury
Condo
9.4Exceptional
(3 Reviews)
2 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $207/Night
7 Nights - US $1,449
Apartment
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $276/Night
7 Nights - US $1,935
House
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $383/Night
7 Nights - US $2,678
House
2 Bedrooms
1 Bath
1 Guest
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $225/Night
7 Nights - US $1,578
Apartment
2.0Average
(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $150/Night
7 Nights - US $1,051
House
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $365/Night
7 Nights - US $2,556
New
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $199/Night
7 Nights - US $1,394
Apartment
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $246/Night
7 Nights - US $1,724
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $99/Night
7 Nights - US $690
Book a Last Minute Place to Stay in Middlebury
About Casai's Private Villas and Holiday Rentals in Middlebury
Discover more than 129 vacation rentals available in Middlebury. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlebury.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlebury, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlebury. On average, places to stay near Middlebury offer 606.46 ft², with nightly prices averaging US $331.
With Casai, finding and comparing holiday rentals in Middlebury is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Middlebury
| Type | Count |
|---|---|
| Vacation Homes | 49 |
| Holiday Apartments | 46 |
| Cottages | 6 |
Use these Quick Filters to Find a Holiday Rental in Middlebury
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Middlebury.
Weather in Middlebury, CT
View the weather forecast for Middlebury before booking your Middlebury Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Middlebury, CT
Casai offers a large selection of top attractions around Middlebury . Research things to do on your vacation before you visit Middlebury.
Other Places to Stay in Middlebury, CT
Frequently Asked Questions About Middlebury?
What are the top holiday rentals in Middlebury?
With numerous options available in Middlebury, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlebury:
- Charming 1760 Cape Nestled in the Foothills of Litchfield County
- Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
- Cozy One Bedroom Apartment Centrally Located in Southbury
- Small Town Stay- Stroll to Local Shops/Dining/Taft
- 6-Acre Luxurious Country Home with Goddess Point Lookout
- Cozy family and pet friendly 3BR Home
- Cozy 1-bedroom apartment in lovely Oxford
- Clean & Bright 2 Bedroom Cottage shares 8 Acres
- Watertown Home w/Yard: 1 Mi to Echo Lake Park!
- Historic Litchfield County Home
How many holiday rentals have private pools in Middlebury?
Discover a selection of holiday rentals with private pools near Middlebury with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Peaceful Oasis in Naugatuck - Charming 3-Bedroom Home with serene backyard.
- Pet-Friendly Woodbury Cottage w/ Fire Pit & Pool!
- Litchfield County home on CT Antiques and CT Wine Trail!
Which holiday homes in Middlebury are best for families?
If you're searching for a family-friendly holiday home in Middlebury, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middlebury:
- Heart of Waterbury. Spacious. New. Office. Parking.
- Private Apartment in Southbury 101
- Comfort Inn Naugatuck-Shelton, CT
How many Casai.com holiday rentals are available in Middlebury?
As of 2026, Casai boasts over 129 properties listed in the Middlebury area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlebury.
People Also Ask
Finding the best prices in Middlebury
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