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Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Aparthotel in The Hill

3.5 star property
9.6 out of 10, Exceptional, (60)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale

Holiday Home in Brookfield

9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Holiday Home in Redding

2.0 star property
10.0 out of 10, Exceptional, (2)
"Several of us stayed for one night for our kids soccer tournament. The home was spacious and had all the amenities needed to make our short stay comfortable. The host was very responsive and accommodating. "
United States
Annette H.
The price is NZ$1,355
includes taxes & fees
15 Dec - 16 Dec
Peaceful Vintage Home with Private Pond in Redding, CT.

Cabin in Northwest Harwinton

8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Holiday Home in New Fairfield

9.2 out of 10, Wonderful, (34)
"Amazing beautiful place!! Everything clean!! Definitely going to come back! "
United States
Andrew E.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Holiday Home in Berlin

2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is NZ$563
includes taxes & fees
30 Nov - 1 Dec
Private Apartment in Berlin

Apartment in Southbury

9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is NZ$229
includes taxes & fees
4 Dec - 5 Dec
New One Bedroom Apartment Centrally Located in Southbury

Apartment in The Hill

10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale

Apartment in Downtown New Haven

9.0 out of 10, Wonderful, (10)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
The price is NZ$392
includes taxes & fees
25 Nov - 26 Nov
Charming Studio| Near Yale| Downtown New Haven

Holiday Home in Plymouth

9.8 out of 10, Exceptional, (39)
"Owners were there, helpful, all in all very good"
United States
Walter B.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Apartment in Wallingford Center

9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
The price is NZ$514
includes taxes & fees
8 Dec - 9 Dec
All New 1BR with tons of Charm

Holiday Home in Danbury

10.0 out of 10, Exceptional, (24)
"We enjoyed a fantastic vacation and the house had amazing views that were fabulous. Plenty of activities for children & adults and the boat rides capped off a perfect week! Sorry to see the week end. "
United States
Jack O.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Apartment in West New Haven

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is NZ$230
includes taxes & fees
25 Nov - 26 Nov
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Aparthotel in The Hill

4.0 star property
9.4 out of 10, Exceptional, (22)
"This was by far the best stay I’ve had in New Haven the apartment was very clean had everything I needed to cook the bed was fabulous had the best sleep not to mention I got to watch the sunset laying down in the bed it was the highlife of my stay loved it I’ve never in my life got to experience laying down in the bed watching the sunset it was great and I’ve been around the world stayed at some great places but never that 💓💓 I will be booking another stay here very soon and the host was so...
United States
Holly
Luxury Apartments by Hyatus at Pierpont

Apartment in East Rock

2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
United States
CHUCK C.
The price is NZ$372
includes taxes & fees
25 Nov - 26 Nov
New Cozy 2BR Stay New Haven Close to Yale

Holiday Home in New Fairfield

10.0 out of 10, Exceptional, (80)
"Beautiful fun home, great owner!"
United States
Robin B.
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Apartment in Cheshire

9.2 out of 10, Wonderful, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$291
includes taxes & fees
25 Nov - 26 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Holiday Home in Shelton

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is NZ$351
includes taxes & fees
25 Nov - 26 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Holiday Home in Northford

10.0 out of 10, Exceptional, (43)
"Perfect!We travel with our large family, several times a year, this is by far the house with the most, everything!Family friendly layout/amenities. The place is beautiful, we will definitely plan to return for a longer stay!And the host is amazing!"
United States
Christina v.
Cozy dog friendly updated house in quiet village adjacent to park

Holiday Home in New Fairfield

9.8 out of 10, Exceptional, (35)
"Beautiful home on Candlewood Lake. Plenty of room for 4 adults and 2 children. Lovely to spend time sitting on the decks or wharf - so relaxing. Hosts very responsive to any questions."
United States
Susan W.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlebury holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as NZ$229 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 holiday 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 holiday.

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 holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What are some of the best holiday rentals that Middlebury has to offer?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: This holiday home rental outside of Middlebury is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Hollow Park and Palace Theatre.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.