Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Our top choices for Middlebury vacation rentals
1. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!3.0 star property
Oakville
The price is NT$8,975
NT$8,975
NT$17,722 total
includes taxes & fees
Nov 16 - Nov 17
2. Las Flores Villa
Las Flores Villa5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
The price is NT$29,441
NT$29,441
NT$47,008 total
includes taxes & fees
Nov 16 - Nov 17
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.
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.
Find vacation rentals that suit your style
Top Middlebury Hotel Reviews
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury DowntownWaterbury
10/10 Excellent
People smoking right outside
People smoking right outside
Courtney
Hampton Inn Waterbury
Hampton Inn WaterburyWaterbury
10/10 Excellent
Lovely victorian decor. Be prepared for a very elevated bed.
Lovely victorian decor. Be prepared for a very elevated bed.
Deborah
The Milestone Inn
The Milestone InnWoodbury
10/10 Excellent
It was so quaint and charming! The room was very clean and generously sized, as was the bed. The fridge and microwave were nice added conveniences. Parking was extremely convenient. Check in was over the phone, which was incredibly easy and quick. I loved everything about the Milestone Inn and look forward to staying there again!
It was so quaint and charming! The room was very clean and generously sized, as was the bed. The fridge and microwave were nice added conveniences. Parking was extremely convenient. Check in was over the phone, which was incredibly easy and quick. I loved everything about the Milestone Inn and look forward to staying there again!
Elin
Heritage Hotel, Golf & Conference Center
Heritage Hotel, Golf & Conference CenterSouthbury
10/10 Excellent
Always a good stay. Been coming to this hotel with the family for at least a decade and I also worked here in my young adult life. The staff is always pleasant, the place is always clean. The pool was a little overcrowded for once and we were given wrist bands for the first time ever. There was a staff member checking we had them on yet 75% of the people there did not have them which I thought was odd. We did not get too enjoy the pool as much as we would have wanted, it’s a great pool but there...
Always a good stay. Been coming to this hotel with the family for at least a decade and I also worked here in my young adult life. The staff is always pleasant, the place is always clean. The pool was a little overcrowded for once and we were given wrist bands for the first time ever. There was a staff member checking we had them on yet 75% of the people there did not have them which I thought was odd. We did not get too enjoy the pool as much as we would have wanted, it’s a great pool but there...
Luz
Comfort Inn Naugatuck-Shelton, CT
Comfort Inn Naugatuck-Shelton, CTNaugatuck
10/10 Excellent
Everything was nice. The only thing they don’t have inside the room is a microwave and the tv need to be update
Everything was nice. The only thing they don’t have inside the room is a microwave and the tv need to be update
Marta
Home2 Suites by Hilton Bristol
Home2 Suites by Hilton BristolBristol
10/10 Excellent
great place
great place
Michelle
Homewood Suites by Hilton Southington, CT
Homewood Suites by Hilton Southington, CTSouthington
10/10 Excellent
Homewood Suites, was a wonderful stay. The location was perfect! For those coffee lovers, Dunkin Donuts is steps aways from the main entrance. Lake Compounce was very close, as well as Target for any last minute items. We also found a great bowling alley and arcade too! The rooms in Homewood Suites exceeded our expectation. They were very big, had a sitting area. We definitely will return!
Homewood Suites, was a wonderful stay. The location was perfect! For those coffee lovers, Dunkin Donuts is steps aways from the main entrance. Lake Compounce was very close, as well as Target for any last minute items. We also found a great bowling alley and arcade too! The rooms in Homewood Suites exceeded our expectation. They were very big, had a sitting area. We definitely will return!
Suzanne Martin
Home2 Suites by Hilton East Haven New Haven
Home2 Suites by Hilton East Haven New HavenThe Centre
10/10 Excellent
One of the best hotels I’ve ever been to
One of the best hotels I’ve ever been to
Daniel
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHGSouthington
10/10 Excellent
Quiet close to espn headquarters
Quiet close to espn headquarters
Steffani
DoubleTree by Hilton Hotel Bristol, Connecticut
DoubleTree by Hilton Hotel Bristol, ConnecticutBristol
10/10 Excellent
The hotel staff very nice, the pool very relaxing, the food was excellent. I will be back.
The hotel staff very nice, the pool very relaxing, the food was excellent. I will be back.
Susan
Cheshire Welcome Inn
Cheshire Welcome InnCheshire
10/10 Excellent
The bed was amazing. The only complaint that I have is that the room that we were in there were lamps on the wall right behind the headboard and I kept hitting my head on one every time I moved on the bed sitting up. Other than that there's a pretty cool place to stay the shower oh my goodness. Somebody needs to get a raise whoever decided to put that shower higher it made it awesome.
The bed was amazing. The only complaint that I have is that the room that we were in there were lamps on the wall right behind the headboard and I kept hitting my head on one every time I moved on the bed sitting up. Other than that there's a pretty cool place to stay the shower oh my goodness. Somebody needs to get a raise whoever decided to put that shower higher it made it awesome.
Benjamin
Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHGSouthington
10/10 Excellent
I liked this hotel. The area was quiet, the staff was professional and the hotel was clean. My only setback was the keycard kept having issues so I had to make trips to front desk. Apart from that, the stay was fine and I would go back. Parking was always available. The hotel sold bkfast and lunches, but also offered free coffee all day. There were food places, including fast foods and diners, that were literally 2‐4 minutes away which was very convenient for the stay.
I liked this hotel. The area was quiet, the staff was professional and the hotel was clean. My only setback was the keycard kept having issues so I had to make trips to front desk. Apart from that, the stay was fine and I would go back. Parking was always available. The hotel sold bkfast and lunches, but also offered free coffee all day. There were food places, including fast foods and diners, that were literally 2‐4 minutes away which was very convenient for the stay.
Constantia
Courtyard by Marriott Southington
Courtyard by Marriott SouthingtonSouthington
10/10 Excellent
This is a nice overall hotel. The area is quiet but there are a couple of restaurants nearby. Rooms are well-furnished and comfortable. I would recommend staying here if you are in the area.
This is a nice overall hotel. The area is quiet but there are a couple of restaurants nearby. Rooms are well-furnished and comfortable. I would recommend staying here if you are in the area.
Christopher
Residence Inn by Marriott New Haven Hamden
Residence Inn by Marriott New Haven HamdenHamden
10/10 Excellent
Ty
Ty
Pam
Quality Inn Waterbury East
Quality Inn Waterbury EastWaterbury
10/10 Excellent
place was a regular hotel
place was a regular hotel
Talli
Courtyard By Marriott Danbury
Courtyard By Marriott DanburyDanbury
10/10 Excellent
Room looked and smelled brand new. Nice modern look
Room looked and smelled brand new. Nice modern look
Laura
Hotel Marcel New Haven, Tapestry Collection By Hilton
Hotel Marcel New Haven, Tapestry Collection By HiltonLong Wharf
10/10 Excellent
Nice property. Surrounding area is not great…
Nice property. Surrounding area is not great…
Matthew
Residence Inn by Marriott Southington
Residence Inn by Marriott SouthingtonSouthington
10/10 Excellent
I liked the distribution of the suite/studio, big enough to move around, have your own space and either sit at the desk to work, cook something or lay in the bed watching the TV that turns to any position in the room.
I liked the distribution of the suite/studio, big enough to move around, have your own space and either sit at the desk to work, cook something or lay in the bed watching the TV that turns to any position in the room.
Anonymous traveler
Find out more about Middlebury
Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:
- View our selection of featured holiday rentals in Middlebury
- Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last
Look no further and take a look at our great range of rental properties in Middlebury!
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 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 Palace Theatre and Beacon Falls Town Recreation Field.
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.