Holiday Rentals Middlebury from £173: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Middlebury holiday rentals

A white house with a wooden staircase leading to a porch.

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Niki B.

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

2. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Watertown

Laurie P.

includes taxes & fees

23 Sept - 24 Sept

A two-story house with a porch, a front door with a wreath, and a small garden area.

3. Bear Retreat - 2-bedroom house in Waterbury

Waterbury

Radha

includes taxes & fees

8 Oct - 9 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

4. Private Apartment in Southbury 103

Southbury

Michael

includes taxes & fees

28 Sept - 29 Sept

A staircase with a handrail, a potted plant with yellow flowers, and a sign above the stairs.

5. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Waterbury

Dirk N.

includes taxes & fees

27 Sept - 28 Sept

A view through a window with a clear sky and lush greenery outside.

6. Private Apartment in Southbury 101

Southbury

Marissa G.

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

7. Stylish Westville Apartment near Yale Campus

West New Haven

Northeast C.

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

8. Once the old Schools house now a newly furnished Apartment

Wallingford Center

Becky P.

includes taxes & fees

24 Sept - 25 Sept

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Top Middlebury Hotel Reviews

Courtyard by Marriott Waterbury Downtown

8/10 Good

"Clean bed Clean bathroom. Some parts of the hotel could use a bit of cleaning and detailing. Parking was easy and inexpensive. The poor lady at the coffee shop could use some help. She was working very hard. Perfume smelling deodorizer is irritating to people with allergies. It burned my eyes."

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as £173 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What are some of the best holiday rentals that Middlebury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Middlebury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Middlebury?

Family-friendly attractions include Quassy Amusement Park, whereas Lake Quassapaug is a spot to enjoy the outdoors. In the wider area, you’ll find Palace Theatre and Beacon Falls Town Recreation Field.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.

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Check prices for these dates

Our top choices for Middlebury holiday rentals

1. Cozy One Bedroom Apartment Centrally Located in Southbury

2. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.