Photo by Brandon Miller

Middlebury Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Middlebury

New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1833)
"Easy parking and safe open area"
The price is CA $142
CA $164 total
includes taxes & fees
Jun 10 - Jun 11
New Haven Village Suites
Lake Luxury
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
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Luxury Furnished Apartments by Hyatus Downtown at Yale
Business centre
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.8 out of 10, Exceptional, (20)
"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
Beautiful cozy rooms near hospital and down town area
Private kitchen
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very good, (10)
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is CA $149
CA $341 total
includes taxes & fees
Jun 17 - Jun 18
Beautiful cozy rooms near hospital and down town area
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
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...
lakefront estate
Pool
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Candlewood Lake Retreat with year round views
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
Spacious Victorian Loft
Fridge, microwave, oven, stovetop
Spacious Victorian Loft
8.4 out of 10, Very good, (6)
"We liked the rental. It was spacious and we appreciated the complimentary coffee. The rental is also a more affordable option in New Haven and not too far away from downtown. It was easy to get in touch with the owner, but it would’ve been helpful if they provided us checkin information in a timely manner. If you’re a light sleeper this might not be the place for you. It’s located by a busy road. There were a lot of cars that were built to be as loud as possible revving their engines into...
The price is CA $131
CA $257 total
includes taxes & fees
Jun 16 - Jun 17
Spacious Victorian Loft
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
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!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (20)
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Property grounds
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, (2)
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is CA $202
CA $429 total
includes taxes & fees
May 31 - Jun 1
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Cozy & Chic Cabin by the Lake, with access to private Beach!
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 CA $273
CA $581 total
includes taxes & fees
May 30 - May 31
Cozy & Chic Cabin by the Lake, with access to private Beach!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
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
Guest Cottage on Country Estate
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Interior
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
9.8 out of 10, Exceptional, (60)
"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!"
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (17)
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Fun Downtown Location
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (48)
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
Don't see what you're looking for?
See all available properties in Middlebury
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

New Haven Hotel
Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1242)
"Very clean and comfortable room. Bed and pillows were very comfortable. Staff on check in and check out were very nice. Only downside is that there is a charge for parking in the garage next door (approx $25) so need to factor that in when comparing hotel prices. "
The price is CA $217
CA $250 total
includes taxes & fees
Jun 2 - Jun 3
New Haven Hotel
Holiday Inn Express Southington, an IHG Hotel
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1001)
"The property was well kept and clean"
The price is CA $197
CA $226 total
includes taxes & fees
May 30 - May 31
Holiday Inn Express Southington, an IHG Hotel
Hilton Garden Inn Shelton
Terrace/patio
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, (1008)
"Friendly environment "
The price is CA $155
CA $179 total
includes taxes & fees
Jun 16 - Jun 17
Hilton Garden Inn Shelton
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.

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury vacation rentals we have selected for you start as low as CA $131 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 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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

5/5 Excellent
"Friendly environment "
A verified traveller stayed at Hilton Garden Inn Shelton
Posted 16 hours ago
Hilton Garden Inn Shelton