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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

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.2 out of 10, Wonderful, (15)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Luxury Apartments by Hyatus at Pierpont
Seasonal outdoor pool

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (18)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (20)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
Exterior

Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

8.8 out of 10, Excellent, (6)
"Very nice property and close to the Shubert Theatre for my event. I would stay at the property again."
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is HK$1,766
HK$2,492 total
includes taxes & fees
23 Jul - 24 Jul
Tranquil Litchfield Connecticut Retreat".
Cozy 3 bedroom minutes from Yale and the beach
Private kitchen

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Fridge, microwave, oven, stovetop

Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa

2.0 star property
6.6 out of 10, (4)
"Communication with the host was excellent. His place was clean, bright, and very well equipped! The location makes it easy to get around the greater Hartford area. Our stay was very good!"
Modern 3BR ★ Fast Wi-Fi + Free Parking ★ Flexible Cancel Anytime! - 10 Mins WeHa
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Property grounds

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (33)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Cozy Cabin @ Sticks & Stones Farm
Interior

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very good, (7)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.2 out of 10, Wonderful, (24)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Spacious Woodbury Home w/ Pool + Hot Tub!
Indoor spa tub

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (2)
"The host was very kind and responsive, which we truly appreciated. However, the house was not properly cleaned. There were a lot of flies inside, the basement had a strong musty smell, and the hot tub water was untreated and had a bad odor, With better cleaning, maintenance, and care for the house the stay could have been much more pleasant."
Spacious Woodbury Home w/ Pool + Hot Tub!
Spectacular Lake front house
Exterior

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "
Spectacular Lake front house
Awesome Lake Home with tons of fun!
Outdoor spa tub

Awesome Lake Home with tons of fun!

2.0 star property
The price is HK$3,532
HK$6,029 total
includes taxes & fees
21 Jul - 22 Jul
Awesome Lake Home with tons of fun!
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (3)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
New One Bedroom Apartment Centrally Located in Southbury
Outdoor dining

New One Bedroom Apartment Centrally Located in Southbury

9.8 out of 10, Exceptional, (6)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is HK$1,060
HK$1,376 total
includes taxes & fees
15 Jul - 16 Jul
New One Bedroom Apartment Centrally Located in Southbury
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
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
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.