Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Middlebury vacation rentals

Interior

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3 reviews)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
$215 nightly
The price is $215
Jan 26 - Jan 27
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Smart TV

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$149 nightly
The price is $168
Feb 25 - Feb 26
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cookware/dishes/utensils

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.8 out of 10, Exceptional, (11 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
$227 nightly
The price is $235
Jan 26 - Jan 27
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
2 bedrooms, WiFi, bed sheets

Vacation Home in Berlin

Private Apartment in Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
$244 nightly
The price is $276
Jan 26 - Jan 27
Total with taxes and fees
Private Apartment in Berlin
Exterior

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$292 nightly
The price is $334
Jan 26 - Jan 27
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Fridge, microwave, oven, stovetop

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
9.4 out of 10, Exceptional, (3 reviews)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
$180 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Interior

Apartment in West New Haven

The Nest At Elm City Flats.
9.6 out of 10, Exceptional, (7 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
$205 nightly
The price is $233
Jan 29 - Jan 30
Total with taxes and fees
The Nest At Elm City Flats.
Fridge, microwave, oven, stovetop

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
$271 nightly
The price is $288
Jan 26 - Jan 27
Total with taxes and fees
All New Studio apartment in center of town
Exterior

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$271 nightly
The price is $288
Jan 26 - Jan 27
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Exterior

Apartment in West Haven

Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
$289 nightly
The price is $327
Jan 26 - Jan 27
Total with taxes and fees
Angelica’s safe haven @ west haven
Interior

Apartment in Southbury

Private Apartment in Southbury 101
9.4 out of 10, Exceptional, (6 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$244 nightly
The price is $276
Feb 2 - Feb 3
Total with taxes and fees
Private Apartment in Southbury 101
Apartment (2 Bedrooms) | Interior

Apartment in West Haven

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
$311 nightly
The price is $358
Jan 26 - Jan 27
Total with taxes and fees
Luxe Living! Apt 1 Mi to West Haven Medical Center
Fridge, microwave, oven, stovetop

Apartment in Southbury

Private Apartment in Southbury 103
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$223 nightly
The price is $252
Jan 26 - Jan 27
Total with taxes and fees
Private Apartment in Southbury 103
WiFi, bed sheets

Apartment in The Hill

2-BR apartment in fantastic New Haven near Yale Hospital and Yale Unv. Apt#9
10.0 out of 10, Exceptional, (1 review)
"It was a lovely place "
United States
Briana B.
$180 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
2-BR apartment in fantastic New Haven near Yale Hospital and Yale Unv. Apt#9
Interior

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 26 - Jan 27
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12 reviews)
"Everything was great and just as charming as the photo indicated. "
United States
Nancy F.
$189 nightly
The price is $189
Jan 26 - Jan 27
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Smart TV

Apartment in Southington

#23 *COMFORT & LUXURY* 3 BR/2 BA House
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$308 nightly
The price is $329
Jan 26 - Jan 27
Total with taxes and fees
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Exterior

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$271 nightly
The price is $288
Jan 26 - Jan 27
Total with taxes and fees
All New 1BR with tons of Charm
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8 reviews)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
Yale Casa Verde Studio
Fridge, microwave, oven, stovetop

Vacation Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
$436 nightly
The price is $494
Jan 26 - Jan 27
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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.
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Top Middlebury Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"The hotel was very clean self parking easy and conveniently located. "
Amber 1-night trip
Posted 2 days ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

Find out more about Middlebury

Everything you need to know about Middlebury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlebury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Middlebury?

Yes, there are vacation rentals in Middlebury close to Quassy Amusement Park, or you can go with a more remote option if you'd like a relaxing place to stay. Middlebury is known for its parks.

What's the top vacation rental in Middlebury?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Middlebury offers a fireplace, a patio, and a barbecue grill 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 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 larger area, you’ll find Waterbury City Hall and Soldiers' Monument.

What’s a vacation rental in Middlebury like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Middlebury. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family getaway.