A weathered stone structure with steps and a small opening, surrounded by fallen leaves and moss.

Middlebury Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Middlebury vacation rentals

Exterior

1. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$108 nightly
The price is $121
Sep 7 - Sep 8
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

2. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very Good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Sep 1 - Sep 2
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Private kitchen

3. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
$254 nightly
The price is $287
Sep 22 - Sep 23
Total with taxes and fees
Private Apartment in Southbury 104
House (3 Bedrooms) | Interior

4. 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
$469 nightly
The price is $539
Sep 14 - Sep 15
Total with taxes and fees
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Private kitchen

5. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.2 out of 10, Wonderful, (5 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$253 nightly
The price is $286
Sep 7 - Sep 8
Total with taxes and fees
Private Apartment in Southbury 103
Interior

6. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$222 nightly
The price is $251
Sep 2 - Sep 3
Total with taxes and fees
Private Apartment in Southbury 101
Room

7. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
$235 nightly
The price is $266
Sep 9 - Sep 10
Total with taxes and fees
Private Apartment in Southbury 105
Interior

8. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (15 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$246 nightly
The price is $278
Aug 31 - Sep 1
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Interior

9. Cozy Studio apartment in delightful Waterbury with Central Air

Cozy Studio apartment in delightful Waterbury with Central Air
Waterbury
$114 nightly
The price is $128
Sep 3 - Sep 4
Total with taxes and fees
Cozy Studio apartment in delightful Waterbury with Central Air
Interior

10. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very Good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
$130 nightly
The price is $147
Aug 31 - Sep 1
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Outdoor dining

11. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$207 nightly
The price is $234
Sep 2 - Sep 3
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Private kitchen

12. #16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT

#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Southington
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay! And happy with most!!!!"
United States
Dawn H.
$553 nightly
The price is $600
Sep 15 - Sep 16
Total with taxes and fees
#16 *A COZY GETAWAY* 4BED/3BATH HOME W/ FIRE PIT
Outdoor dining

13. Lakehaven • Hot Tub, Decks, Fires & More

Lakehaven • Hot Tub, Decks, Fires & More
Plymouth
$898 nightly
The price is $1,016
Aug 31 - Sep 1
Total with taxes and fees
Lakehaven • Hot Tub, Decks, Fires & More
Exterior

14. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (7 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
$297 nightly
The price is $336
Aug 31 - Sep 1
Total with taxes and fees
Angelica’s safe haven @ west haven
Interior

15. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
$209 nightly
The price is $237
Sep 2 - Sep 3
Total with taxes and fees
Private Apartment in Southbury 102
Apartment (1 Bedroom) | Interior

16. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
$244 nightly
The price is $280
Sep 1 - Sep 2
Total with taxes and fees
Bristol Condo Near Espn HQ & Lake Compounce!
Exterior

17. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
$278 nightly
The price is $296
Aug 31 - Sep 1
Total with taxes and fees
All New 1BR with tons of Charm
Living area

18. #43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
$474 nightly
The price is $511
Sep 7 - Sep 8
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat | Fire Pit
Room

19. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$278 nightly
The price is $296
Aug 31 - Sep 1
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Private kitchen

20. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
$398 nightly
The price is $398
Aug 31 - Sep 1
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
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

New Haven Hotel

New Haven Hotel

8/10 Good
"Very spacious room. Tired and a bit musty but clean and well-maintained. Lots of room to spread out; bathroom more than adequate. I really appreciated the enclosed, secure garage so close with the use of the footbridge. I do wish I'd been told I needed my room key to get out of the garage - I'd already turned it in. If it wasn't for the parking attendant letting me out, I'd have been stuck running across the street to get my key back from the front desk, all while blocking the exit."
Lauren 1-night trip
Posted 11 hours ago
New Haven Hotel

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 $246 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?

Cozy 1-bedroom house in lovely New Haven with AC close to Yale University: This vacation home rental near Middlebury is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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.