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Middlebury Holiday Rentals

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Check prices for these dates

Tonight
14 Jul - 15 Jul
Tomorrow
15 Jul - 16 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Middlebury

Private Apartment in Berlin
Fridge, microwave, oven, stovetop

Private Apartment in Berlin

2.0 star property
10.0 out of 10, Exceptional, (4)
"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. "
The price is HK$1,181
HK$3,424 total
includes taxes & fees
16 Jul - 17 Jul
Private Apartment in Berlin
Once the old Schools house now a newly furnished Apartment
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

9.0 out of 10, Wonderful, (12)
"The place was perfect for a quick weekend trip back to our hometown."
The price is HK$858
HK$2,203 total
includes taxes & fees
20 Jul - 21 Jul
Once the old Schools house now a newly furnished Apartment
New! Trail-side Haven Retreat! Pet friendly
Beach

New! Trail-side Haven Retreat! Pet friendly

9.4 out of 10, Exceptional, (8)
"Clean and comfortable, in a quiet area. Prefect for a family gathering"
The price is HK$863
HK$2,674 total
includes taxes & fees
16 Jul - 17 Jul
New! Trail-side Haven Retreat! Pet friendly
Beautiful cozy home w jacuzzi & dock for boat
Terrace/patio

Beautiful cozy home w jacuzzi & dock for boat

The price is HK$2,253
HK$4,977 total
includes taxes & fees
28 Jul - 29 Jul
Beautiful cozy home w jacuzzi & dock for boat
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fridge, microwave, oven, coffee/tea maker

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

7.6 out of 10, Good, (5)
"This was a 2 month stay for us and was not equipped for longer term stays. Storage is a challenge. On the plus side, the host is responds quickly and helped with any issues we had. The location was great as we needed to be in a specific area."
The price is HK$1,680
HK$2,787 total
includes taxes & fees
11 Aug - 12 Aug
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

9.6 out of 10, Exceptional, (13)
"The apartment was beautiful. One highlight for the children was the arcade game in the living room. The view of the water was striking from the living room and bedroom. The neighborhood was very quiet. Shakeema was a great host, easy to contact and she responds quickly. Thank you! I would recommend this VRBO to family and friends."
The price is HK$2,276
HK$3,733 total
includes taxes & fees
15 Jul - 16 Jul
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Interior

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

The price is HK$4,710
HK$7,316 total
includes taxes & fees
21 Jul - 22 Jul
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Heavenly Home in New Haven /5 mins drive from Yale
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

9.0 out of 10, Wonderful, (19)
"Place was so cute and spacious. Owner was awesome too! Definitely recommend."
The price is HK$5,761
HK$8,023 total
includes taxes & fees
15 Jul - 16 Jul
Heavenly Home in New Haven /5 mins drive from Yale
Stocked home close to Yale, in Heart of New Haven
Fridge, microwave, oven, stovetop

Stocked home close to Yale, in Heart of New Haven

9.0 out of 10, Wonderful, (16)
"We loved our stay. It was just as expected and the host is responsive and friendly"
The price is HK$1,166
HK$1,987 total
includes taxes & fees
15 Jul - 16 Jul
Stocked home close to Yale, in Heart of New Haven
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
Outdoor dining

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
The price is HK$1,444
HK$3,284 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds

9.0 out of 10, Wonderful, (8)
"the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!"
The price is HK$1,672
HK$3,622 total
includes taxes & fees
22 Jul - 23 Jul
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking
Fridge, microwave, oven, stovetop

Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking

9.8 out of 10, Exceptional, (10)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
The price is HK$1,648
HK$3,619 total
includes taxes & fees
13 Aug - 14 Aug
Casa Soleada in East Rock |King Bed| Near DT and Yale SOM | Free parking
Modern apt in Wooster Square
Property grounds

Modern apt in Wooster Square

10.0 out of 10, Exceptional, (1)
"Very clean property. Location is fabulous. The host was very easy to communicate with. This was the second time we stayed at this place and were very happy both times. "
The price is HK$777
HK$2,457 total
includes taxes & fees
15 Jul - 16 Jul
Modern apt in Wooster Square
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
Interior

Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven

The price is HK$1,005
HK$2,060 total
includes taxes & fees
15 Jul - 16 Jul
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
Westshore Luxury
Outdoor dining

Westshore Luxury

7.0 out of 10, Good, (4)
"Check-in time was at 12 noon. House was not clean, was asked to come back 3 hours later. Contact property manager, they said to contact the vacation rental company We chose this place because check-in was supposed to be at 12pm as listed but it was not ready at12 o'clock. That was the reason why we chose that place. Because we had a wedding to be at 4 and we wanted Get dressed at rental property. Was explain this to the property manager? Not only the day of but the day before, reminding her...
The price is HK$3,917
HK$5,309 total
includes taxes & fees
28 Jul - 29 Jul
Westshore Luxury
The Santiago in Science Park at Yale New Haven
Exterior detail

The Santiago in Science Park at Yale New Haven

8.6 out of 10, Excellent, (7)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
The price is HK$973
HK$1,782 total
includes taxes & fees
23 Jul - 24 Jul
The Santiago in Science Park at Yale New Haven
3-bedroom house just walking distance from Yale and Downtown
Terrace/patio

3-bedroom house just walking distance from Yale and Downtown

The price is HK$1,766
HK$3,287 total
includes taxes & fees
16 Jul - 17 Jul
3-bedroom house just walking distance from Yale and Downtown
Near Yale with Game Room
Fridge, microwave, oven, stovetop

Near Yale with Game Room

The price is HK$3,787
HK$8,441 total
includes taxes & fees
15 Jul - 16 Jul
Near Yale with Game Room
Welcome to your dream retreat!
Fridge, microwave, oven, dishwasher

Welcome to your dream retreat!

8.0 out of 10, Very good, (1)
"Close to Westville shopping, Yale athletic fields/stadiums, events at SCSU, or a short drive or bus ride to downtown, Beaver Hill is a great neighborhood. I rented this property for overflow family in town for a wedding. The house is very clean and nicely appointed. While I would have like to see some cooking equipment (we're a family that likes to cook), I believe the owner has addressed this concern. This is a nice, comfortable, clean place perfect for a family. I would definitely rent...
The price is HK$3,132
HK$5,550 total
includes taxes & fees
10 Aug - 11 Aug
Welcome to your dream retreat!
New Haven Staycation|Near Yale|Washer/Dryer|Groups
TV, fireplace

New Haven Staycation|Near Yale|Washer/Dryer|Groups

The price is HK$3,360
HK$5,738 total
includes taxes & fees
3 Aug - 4 Aug
New Haven Staycation|Near Yale|Washer/Dryer|Groups
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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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?

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!: This holiday home rental outside of Middlebury is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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 Whittemore Glen State Park and Waterbury City Hall.

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.