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Middlebury Vacation Rentals

Vacation Rentals in Middlebury

Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Business center
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (18)
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Smart TV, fireplace, table tennis, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, (11)
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
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Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (71)
"Great place to celebrate a 40th birthday. Place was clean and comfortable. Great view. Hot tub, lawn games, movie theater, pool table, and more were all great."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (19)
"We had such a relaxing, wonderful stay at this lakefront oasis. The lake views from the upstairs living room & the downstairs kitchen and yard were lovely. The number of song birds was delightful to watch and hear. We counted 31 birds in <1 hour! We also saw turtles, fish, and a Bald Eagle."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (7)
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is $200
$426 total
includes taxes & fees
May 20 - May 21
Cozy & Chic Cabin by the Lake, with access to private Beach!
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (40)
"We were in town to celebrate my son's college graduation, and stayed at this beautiful home about 30 minutes from Quinnipiac University. The house was very clean and the check in process was smooth. Stacie was extremely responsive to our inquiries, despite being on vacation in a different time zone. The sitting room area overlooked the Long Island sound, and the master bedroom and kitchen also had beautiful views. The house was stocked with some board games, and also outdoor games (Spikeball,...
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (16)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (17)
"We had a wonderful stay in the house. It has incredible views and the lake is beautiful."
The price is $465
$945 total
includes taxes & fees
May 23 - May 24
Lakeview Estate - Chef's Kitchen - NYC Getaway
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, (2)
"Was perfect for my family of 8 for the few days we were in New Haven for my PA graduation. Close to all main dining ! Host was very responsive on all questions I had !"
The price is $293
$624 total
includes taxes & fees
May 28 - May 29
New Haven Oasis: Steps to Yale & Fine Dining
Smart TV, fireplace, offices
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"Cute."
The price is $140
$214 total
includes taxes & fees
May 19 - May 20
Peaceful apartment on 3.5 acres w/ artist studio.
Fridge, microwave, oven, stovetop
Stunning Apt W/ Parking and Gym | Downtown at Yale
10.0 out of 10, Exceptional, (27)
"Easy access and quick to get in and out. Nice apartment. Matched pictures and expectations."
Stunning Apt W/ Parking and Gym | Downtown at Yale
Interior
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
9.8 out of 10, Exceptional, (59)
"Located close to everything you need and in a quiet location close to the Yale Campus.....one of our favorite places to stay when we are in town!"
The price is $147
$293 total
includes taxes & fees
May 22 - May 23
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Property grounds
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
9.8 out of 10, Exceptional, (36)
"nice place in New Haven"
The price is $147
$466 total
includes taxes & fees
Jun 5 - Jun 6
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (47)
"Host was amazing 5 star all the way ... we walked right down the street and had some pizza everything we needed was just around the corner."
Fun Downtown Location
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (20)
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Fridge, microwave, oven, stovetop
Historic Whitneyville Cottage
9.6 out of 10, Exceptional, (10)
"We have stayed in this little cottage several times now. Convenient location for visiting downtown New Haven. Bed is comfortable - kitchen small but it has what you need. Nice walking neighborhood if you have dogs. We will be back."
Historic Whitneyville Cottage
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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.

Other types of properties in Middlebury you may be interested in

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 $96 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.

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?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This vacation home rental near Middlebury is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

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 Hop Brook Lake and Union Station Clocktower.

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.

Recent reviews of Middlebury properties
Expedia verified reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

5/5 Excellent
Great
"My stay was loveky"
A verified traveler stayed at Omni New Haven Hotel at Yale
Posted 16 hours ago
Omni New Haven Hotel at Yale