Title: Middlebury Vacation Rentals from CA $165: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlebury vacation rentals

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/09be7b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/b812e781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/c0cd40cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122120000/122111200/122111158/bf86c795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Living! Apt 1 Mi to West Haven Medical Center

[](https://www.expedia.ca/West-Haven-Hotels-2-Mi-To-Beach.h122111158.Hotel-Information)

West Haven

CA $188

CA $491 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/West-Haven-Hotels-2-Mi-To-Beach.h122111158.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/4172866e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/27201c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/dc603626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/e15142a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

[](https://www.expedia.ca/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.Hotel-Information)

Oakville

CA $251

CA $641 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22&regionId=183065&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America&regionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN)

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## Top Middlebury Hotel Reviews

![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg)

### New Haven Hotel

10/10 Excellent

"Excellent desk staff. Clean and quite room. Good location."

[](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information)

![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg)

### Hyatt Place Milford / New Haven

10/10 Excellent

"Room was spotless the staff was amazing. Room fully stocked with amenities. Had a great stay! The only down side was there were no microwaves in the rooms."

[](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information)

![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg)

### Courtyard by Marriott Waterbury Downtown

10/10 Excellent

"All of the above "

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information)

![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg)

### The Farmington Inn & Suites

10/10 Excellent

"From desk staff "

[](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information)

![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg)

### Homewood Suites by Hilton Orange New Haven

10/10 Excellent

"Omg. Where do I start? What impressed me the most was the welcoming staff. Upon arriving in my room, the televisions displayed a personalized welcome message with my name, which was cool. My room was magnificent! Beautiful. Modern. Very clean. Smelled wonderful!"

[](https://expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information)

![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg)

### Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent

"Good hotel every clean 😍"

[](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information)

![Courtyard by Marriott New Haven Orange-Milford](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/bdad3f31_y.jpg)

### Courtyard by Marriott New Haven Orange-Milford

10/10 Excellent

"People were nice, room was clean and spacious. Bed was a little soft and breakfast choices were little limited. But overall great stay at a great price."

[](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information)

![Hamden Hotel and Suites – Hamden New Haven](https://images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg)

### Hamden Hotel and Suites – Hamden New Haven

10/10 Excellent

"The rooms are very neat, and the workers are courteous and helpful "

[](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information)

![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg)

### Omni New Haven Hotel at Yale

10/10 Excellent

"staff was terrific gentleman at the front desk (on 12/31/25) - I don’t recall his name but was super kind"

[](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information)

## Find out more about Middlebury

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlebury. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Middlebury ](https://expedia.ca/Middlebury-Private-Vacation-Homes.d183065-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Middlebury ](https://expedia.ca/Middlebury-Apartments.d183065-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Middlebury ](https://expedia.ca/Middlebury-Cottages.d183065-aaCottages.Travel-Guide-Accommodation)
- [Motels in Middlebury ](https://expedia.ca/Middlebury-Motels.d183065-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Middlebury ](https://expedia.ca/Middlebury-Cabins.d183065-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Middlebury ](https://expedia.ca/Middlebury-Guest-Houses.d183065-aaGuestHouses.Travel-Guide-Accommodation)
- [Condo Rentals in Middlebury ](https://expedia.ca/Middlebury-Condos.d183065-aaCondos.Travel-Guide-Accommodation)
- [Farmstay in Middlebury ](https://expedia.ca/Middlebury-Agritourism.d183065-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Middlebury ](https://expedia.ca/Middlebury-Bed-And-Breakfast.d183065-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Aparthotels in Middlebury ](https://expedia.ca/Middlebury-Apart-Hotels.d183065-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Middlebury ](https://expedia.ca/Middlebury-Villas.d183065-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Middlebury ](https://expedia.ca/Middlebury-Lodges.d183065-aaLodges.Travel-Guide-Accommodation)
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## Frequently asked questions

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