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Middlebury Vacation Rentals

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Our top choices for Middlebury vacation rentals

Interior
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (3)
"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.
$224 nightly
The price is $224
Jan 13 - Jan 14
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
10.0 out of 10, Exceptional, (21)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$112 nightly
The price is $126
Jan 11 - Jan 12
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (14)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Jan 14 - Jan 15
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 9 - Jan 10
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Great location, exactly as advertised. The shades are somewhat translucent, so a bit bright at night, but wore a mask and it was fine. "
United States
Scott B.
$178 nightly
The price is $178
Jan 11 - Jan 12
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop
One bedroom apartment in United States of America, New Haven

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
9.4 out of 10, Exceptional, (3)
"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.
$182 nightly
The price is $206
Jan 11 - Jan 12
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
TV
Newly Remodeled with deck. Close to town center

Apartment in Wallingford

Newly Remodeled with deck. Close to town center
10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$273 nightly
The price is $290
Jan 9 - Jan 10
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Interior
All New Studio apartment in center of town

Apartment in Wallingford Center

All New Studio apartment in center of town
10.0 out of 10, Exceptional, (2)
"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.
$273 nightly
The price is $290
Jan 9 - Jan 10
Total with taxes and fees
All New Studio apartment in center of town
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.8 out of 10, Exceptional, (11)
"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.
$273 nightly
The price is $285
Jan 12 - Jan 13
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$266 nightly
The price is $283
Jan 31 - Feb 1
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Interior
Private Apartment in Berlin

Vacation Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"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.
$266 nightly
The price is $301
Jan 11 - Jan 12
Total with taxes and fees
Private Apartment in Berlin
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
9.6 out of 10, Exceptional, (4)
"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.
$303 nightly
The price is $347
Jan 11 - Jan 12
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Dining
Spacious 2 Bedroom apartment close to Yale Bowl

Apartment in West New Haven

Spacious 2 Bedroom apartment close to Yale Bowl
9.6 out of 10, Exceptional, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
$203 nightly
The price is $230
Jan 9 - Jan 10
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
Desk, iron/ironing board, WiFi, bed sheets
Yale Casa Verde Studio

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Jan 9 - Jan 10
Total with taxes and fees
Yale Casa Verde Studio
Interior
The Nest At Elm City Flats.

Apartment in West New Haven

The Nest At Elm City Flats.
9.4 out of 10, Exceptional, (6)
"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.
$210 nightly
The price is $238
Jan 11 - Jan 12
Total with taxes and fees
The Nest At Elm City Flats.
Interior
Private Apartment in Southbury 101

Apartment in Southbury

Private Apartment in Southbury 101
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
$244 nightly
The price is $276
Jan 14 - Jan 15
Total with taxes and fees
Private Apartment in Southbury 101
Apartment (2 Bedrooms) | Interior
2 Mi to Beach, Shared Yard Space: West Haven Apt!

Apartment in West Haven

2 Mi to Beach, Shared Yard Space: West Haven Apt!
3.0 star property
$311 nightly
The price is $358
Jan 11 - Jan 12
Total with taxes and fees
2 Mi to Beach, Shared Yard Space: West Haven Apt!
Exterior
Angelica’s safe haven @ west haven

Apartment in West Haven

Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (6)
"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
$279 nightly
The price is $317
Jan 9 - Jan 10
Total with taxes and fees
Angelica’s safe haven @ west haven
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
$283 nightly
The price is $321
Jan 12 - Jan 13
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$174 nightly
The price is $197
Jan 11 - Jan 12
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Good"
Joon Young 2-night trip
Posted 2 days ago
Best Western Executive Hotel Of New Haven - West Haven

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 $163 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 Palace Theatre.

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.