Photo by Brandon Miller

Middlebury holiday rentals

We found 149 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Middlebury to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Middlebury

Showing deals for:1 Jan - 8 Jan

3rd sleeping area with ground-floor walkout
Summer; forest view
Winter; main room
Entrance
Exceptional
(8 reviews)

Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes

Waterbury

8% off
AU$4,150
for 7 nights, 1 cabin
AU$593 per night
includes taxes & fees
Peaceful Wooded Retreat – Quiet Escape, Close to Wolcott Lakes
Private kitchen
Gorgeous sunsets every night
Steam shower
Movie room with 85" 4k screen and surround sound Sonos System
Exceptional
(56 reviews)

Litchfield County Four Season Country Paradise

Roxbury

8% off
AU$11,908
for 7 nights, 1 home
AU$1,701 per night
includes taxes & fees
Litchfield County Four Season Country Paradise
Private kitchen
Property grounds
Living area
Terrace/patio
Exceptional
(16 reviews)

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown

8% off
AU$2,139
for 7 nights, 1 cottage
AU$306 per night
includes taxes & fees
Cozy cottage with AC and lake access in charming Connecticut suburb.
Kitchen
Sunset
Living Room
Bedroom 1: King
Exceptional
(10 reviews)

6-Acre Luxurious Country Home with Goddess Point Lookout

Woodbury

8% off
AU$18,207
for 7 nights, 1 home
AU$2,601 per night
includes taxes & fees
6-Acre Luxurious Country Home with Goddess Point Lookout
Exterior
Kitchen fun afternoon tea fundraiser for Woodbury's Food Bank.
Property grounds
The skylighted kitchen
Exceptional
(59 reviews)

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Woodbury

12% off
AU$3,957
for 7 nights, 1 home
AU$565 per night
includes taxes & fees
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants
Outdoor dining
Interior
Interior
Living area
Exceptional
(52 reviews)

Beach, Paddle Boards. Swim

Bethlehem

7% off
AU$2,517
for 7 nights, 1 cabin
AU$360 per night
includes taxes & fees
Beach, Paddle Boards. Swim
New refrigerator, microwave, air fryer, coffee maker 2022
small, covered front porch on cottage
Interior
Lovely rolling 8 Acre farmland is shared with the main house
Exceptional
(9 reviews)

Clean & Bright 2 Bedroom Cottage shares 8 Acres

Southbury

16% off
AU$2,169
for 7 nights, 1 cottage
AU$310 per night
includes taxes & fees
Clean & Bright 2 Bedroom Cottage shares 8 Acres
Interior
Private kitchen
Dining
Room
Very good
(9 reviews)

Excellent Home Away From Home

Waterbury

15% off
AU$2,192
for 7 nights, 1 home
AU$313 per night
includes taxes & fees
Excellent Home Away From Home
Private kitchen
Interior
Property grounds
Exterior
Exceptional
(5 reviews)

The Perch in the Purchase -- Cozy, unique, and private

Southbury

8% off
AU$1,726
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
The Perch in the Purchase -- Cozy, unique, and private
Living Room
View of the Pond
Bathroom
Kitchen
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,140
for 7 nights, 1 apartment
AU$306 per night
includes taxes & fees
Private Apartment in Southbury 101
Queen Bedroom
Open Concept Living Room, Dining Room, Kitchen
Dining Room
Outdoors
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

7% off
AU$1,953
for 7 nights, 1 apartment
AU$279 per night
includes taxes & fees
Private Apartment in Southbury 102

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Middlebury getaway

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Middlebury. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Middlebury

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Middlebury a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Quassy Amusement Park (1.2 mi / 1.9 km)
  • The Christmas Shop (8.6 mi / 13.8 km)
  • Mount Southington Ski Area (11.1 mi / 17.9 km)
  • Lake Compounce (13 mi / 20.9 km)
  • Yale Golf Course (16.2 mi / 26.1 km)
  • Hopkins Vineyard (16.9 mi / 27.2 km)

Exploring the natural features in Middlebury

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Middlebury is a great place to get outside. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Waterbury Green (4.9 mi / 7.9 km)
  • Beacon Falls Town Recreation Field (6.4 mi / 10.3 km)
  • Lake Lillinonah (11.4 mi / 18.4 km)
  • Steep Rock Preserve (12.1 mi / 19.5 km)
  • Bantam Lake (13.1 mi / 21.1 km)
  • Mount Carmel (13.5 mi / 21.8 km)

Travelling to and around Middlebury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 3.5 mi (5.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 21.4 mi (34.5 km) away.

Frequently asked questions

What is the best area to stay in Middlebury when booking a holiday rental?
When considering a holiday rental in Middlebury, Connecticut, a popular area to stay is near the picturesque Middlebury Green. This charming neighbourhood offers a lovely blend of suburban tranquillity and convenient access to local amenities. The area features a variety of properties, ranging from quaint cottages to more spacious family homes, making it an excellent choice for different types of travellers.Just a short distance away, you can explore the stunning Lake Quassapaug, which is great for outdoor enthusiasts looking to enjoy activities such as swimming, fishing, or simply basking in the beautiful scenery. Additionally, the nearby Flanders Nature Centre provides lovely trails and educational programmes, making it a fantastic spot for families and nature lovers alike.
What is the most popular type of holiday rental accomodation in Middlebury?
In Middlebury, apartments are the most popular type of holiday rental, with several available throughout the area. These rentals typically offer modern amenities, including fully equipped kitchens, comfortable living spaces, and some may feature outdoor areas for relaxation. Positioned in quiet neighbourhoods, they provide guests with a homely atmosphere while being conveniently located for exploring the charming surroundings of Connecticut.
What are popular rental amenities in Middlebury?
In Middlebury, popular rental amenities include outdoor spaces such as decks and patios, which are superb for enjoying the tranquil surroundings. Many holiday rentals also offer onsite parking, making it convenient for guests travelling by car.
When is the best time to visit Middlebury for a holiday rental?
The peak season for visiting Middlebury is from May to July, when the landscape bursts into life and the weather is at its most pleasant. This period is ideal for travellers who enjoy outdoor activities, as it offers a variety of options for hiking, cycling, and exploring the picturesque surroundings. With temperatures typically ranging from 15 to 30 degrees Celsius, you can comfortably engage in sightseeing and leisurely strolls through the charming town.July stands out as the most popular month to visit, drawing in families and adventure seekers eager to make the most of the summer sun. Visitors can enjoy local events, farmers' markets, and the vibrant community spirit that defines Middlebury during this lively time.For those looking for more affordable options, consider planning your trip in December. Although this month is less crowded, it presents a unique opportunity to experience Middlebury's winter charm, with cosy gatherings and holiday festivities that add a special touch to your stay.Ultimately, the best time to book a holiday rental in Middlebury hinges on your preferences—whether you favour the bustling summer months filled with outdoor adventures or the tranquil beauty of a winter visit.
What are the top attractions in Middlebury?
In Middlebury, Connecticut, visitors can enjoy a range of attractions that highlight the area's natural beauty and local charm. The stunning Lake Quassapaug is a popular spot for outdoor activities, including swimming, fishing, and boating, making it a lovely destination for families and nature enthusiasts. Nearby, the Quassapaug State Park offers scenic walking trails and picnic areas, great for a relaxing day out.For those interested in history, the Middlebury Historical Society showcases the town's rich heritage, with exhibits and events that reflect its past. The nearby Mattatuck Museum, located in Waterbury, features a diverse collection of art and historical artifacts, providing a deeper insight into the region's cultural landscape.In addition, the picturesque Woodbury town centre, just a short drive away, is known for its antique shops, art galleries, and charming cafes, offering visitors a delightful experience of local shopping and dining.
Are all fees included in the Middlebury holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Middlebury holiday homes with parking?
Stayz offers a wide selection of holiday homes in Middlebury with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Middlebury holiday homes?
You can find great discounts on holiday homes in Middlebury on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Middlebury holiday home booking on Stayz?
To find Middlebury holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middlebury?
A long-stay holiday home in Middlebury is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Middlebury holiday home?
Book your Middlebury holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middlebury?
Prices for holiday homes in Middlebury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Middlebury to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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