Photo by Brandon Miller

Holiday Rentals in Middlebury

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Holiday Rentals in Middlebury

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2006)
"Easy fast check in"
The price is €96
includes taxes & fees
4 Mar - 5 Mar
New Haven Village Suites

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (39)
"I was completely satisfied with my stay. Apartment had wonderful amenities and an amazing view. Great location near downtown restaurants too."
Luxury Furnished Apartments by Hyatus Downtown at Yale

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

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

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

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

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Cozy Cabin @ Sticks & Stones Farm

8.0 out of 10, Very good, (2)
"If you pictured this property minutes from the historic district of Newtown it’s exactly that. The space brings to life the feeling of the rustic yet comfortable aspect of Connecticut. My adult son and teenage daughter were comfortable but thoroughly enjoyed the living room fireplace. This location is 10 minutes away from restaurants that will please most families with a mix of family to high end with a side of fancy. "
The price is €185
includes taxes & fees
3 Mar - 4 Mar
Cozy Cabin @ Sticks & Stones Farm

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (22)
"Mariana is a wonderful host. She communicates well and is very efficient in responding to any questions or inquiries you may have.The cabin is very clean, and has just about everything you would need. We really enjoyed using the fireplace! 10/10 recommend. "
Cozy & Chic Cabin by the Lake, with access to private Beach!

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (13)
"Great. Would prefer to anyone"
Luxury Apartments by Hyatus at Pierpont

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

10.0 out of 10, Exceptional, (3)
"First time booking and the place was perfect, beautiful views, real cozy vibes, and the host did a great job to attend at anything we needed "
NEW! LAKE FRONT, Private Dock, Fire Pit, Paddle Boards, Kayaks & Rec Room!

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
"This place is amazing!! The house had everything we needed and more. We really enjoyed our stay and also be able to host some of our family in the area was precious. My daughters rented equipment for the babies which worked out well. The house is very spacious and 5 adults and 3 children fit nicely. Very highly recommend. The pier was fun to hang out on but due to weather we were to enjoy the lake as much. Easy to find, and owners were very responsive. "
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Heavenly Home in New Haven

8.8 out of 10, Excellent, (18)
"I needed a large space for my bridesmaids to stay and get our makeup done for the wedding and have a casual rehearsal dinner. This house was perfect. The neighborhood looks a little sketchy but we had no problems at all. Didn’t hear any noise. The only thing that I would say is that the couches were a little worn and could use a good shampooing. The floors also weren’t very clean. After walking around our socks were black. I would still recommend this house for large groups."
The price is €585
includes taxes & fees
1 Mar - 2 Mar
Heavenly Home in New Haven

Luxurious 3BR Apartment with Premium Amenities

9.8 out of 10, Exceptional, (6)
"Apartment was immaculate. Easy check-in process and Hyatus was communicative, friendly, and helpful. Furniture in the living area is a little cramped but for just a few days it was all we needed! Noise level wasn't bad, but the windows are not soundproof so we could hear the occasional siren (it's very close to the hospital). But the building itself was fairly quiet. My only negative feedback: while 2 of the beds were comfortable, the third one was very clearly not a mattress at all, just a box...
Luxurious 3BR Apartment with Premium Amenities
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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Other types of properties in Middlebury you may be interested in

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1467)
"Staff is always super friendly. Nice area with convenient parking. I have stayed here several times with my husband and as a single female traveler and always feel safe and comfortable."
The price is €129
includes taxes & fees
11 Mar - 12 Mar
New Haven Hotel

Omni New Haven Hotel at Yale

4.0 star property
8.2 out of 10, Very good, (1002)
"Everything was great except for the noise from the nightclub accross the street."
The price is €165
includes taxes & fees
12 Mar - 13 Mar
Omni New Haven Hotel at Yale

Trumbull Marriott Shelton

3.5 star property
8.2 out of 10, Very good, (1000)
"Excellent service! "
The price is €142
includes taxes & fees
9 Mar - 10 Mar
Trumbull Marriott Shelton
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.

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; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!: This holiday home rental outside of Middlebury is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Hop Brook Lake 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.