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Compare 254 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Renovated, one level home in an excellent location
Fully equipped kitchen. (1)

Renovated, one level home in an excellent location

10.0 out of 10, Exceptional, (38)
"3 college roommates stayed because new Milford was a convenient location for all 3 of us. Great girls trip catching up with wine snacks and movies. We weren’t familiar with the area so wished we would have stayed closer to town aka the Green but it was nice to have a 5 minute walk down to the little private beach area and an easy 10ish minute drive to town to walk around some shops before heading back to enjoy good company. Thanks Alberto! U were great with ur communication both before and...
Renovated, one level home in an excellent location
Room in Apartment - Plaid Room 3min From Yale Univ
Room

Room in Apartment - Plaid Room 3min From Yale Univ

3.0 star property
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
Room in Apartment - Plaid Room 3min From Yale Univ
Family Gem on Dyer Street

Family Gem on Dyer Street

10.0 out of 10, Exceptional, (2)
"Needed a place to stay for the night and it was just the perfect spot. The house was just as it seemed online and it was a lot bigger than I expected. Everything was really nice and the host was super nice and very easy to communicate with. Would 100% recommend to others for their next stay."
The price is AED 727
AED 1,443 total
includes taxes & fees
22 Jan - 23 January 2025
Family Gem on Dyer Street
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (78)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Home on the sound
Room

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Charming 1870 cape cottage in Litchfield
Outdoor dining

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (40)
"Beautiful property. Super clean. Wish we could have stayed longer."
Charming 1870 cape cottage in Litchfield
Ranch style living at its best with country garden & patio!
Room

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
The Santiago in Science Park at Yale New Haven
Living area

The Santiago in Science Park at Yale New Haven

9.6 out of 10, Exceptional, (4)
"The property had everything needed and was a short distance to so many campus sites. Would definitely stay again."
The price is AED 349
AED 628 total
includes taxes & fees
22 Jan - 23 January 2025
The Santiago in Science Park at Yale New Haven
Near Yale 8 beds Gaming Room
Exterior

Near Yale 8 beds Gaming Room

The price is AED 1,969
AED 3,968 total
includes taxes & fees
2 Jan - 3 January 2025
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
Exterior detail

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Exterior

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
The Candlewood Lake Retreat - Private Dock & Pool

The Candlewood Lake Retreat - Private Dock & Pool

The Candlewood Lake Retreat - Private Dock & Pool
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Exterior

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

9.8 out of 10, Exceptional, (26)
"The view in the fall was amazing! So relaxing to sit and watch the lake while having our coffee. The owners are amazing. Everything we needed and more. Plenty of room for the family or even if multiple families stayed. Would stay here again!"
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Cottage at Sunny Day, multiple levels for multiple views of the lake

Stay 3 Nights or Longer Until January 31 and Get 15% Off

9.8 out of 10, Exceptional, (29)
"The place has stunning views from just about every window. Taunton Lake is so serene and the surrounding area has so much local charm. The beds were comfy and the amenities were abundant. I hope to be back again someday."
Stay 3 Nights or Longer Until January 31 and Get 15% Off
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (24)
"Fantastic place! Beautiful views, lots of room, comfy beds, clean. There was 10 of us and it was a delight. Highly recommend it. "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Exterior

Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!

10.0 out of 10, Exceptional, (11)
"This was just what we were looking for. The house was roomy, open and charming. It was also relaxing to sit on the back deck surrounded by trees and listening to the calming sound of the brook. It felt like you out in the countryside yet the cute village of Sandy Hook along with Newtown restaurants and shopping were less than 10 minutes away."
Wooded Getaway on Serene Brook ~ 50 Acres of Privacy!
Traveling Nurse or Business Professional
Exterior

Traveling Nurse or Business Professional

10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Terrace/patio

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (14)
"Beautiful property— even more than the pictures (which is often rare). Quiet, scenic, and spacious. Communication with the host was very good and helpful."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Property grounds

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

9.0 out of 10, Wonderful, (6)
"We had a wonderful time. Quiet and pleasant "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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 property types in Middlebury

New Haven Village Suites
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1985)
"One of our favorites"
The price is AED 360
AED 414 total
includes taxes & fees
29 Dec - 30 Dec
New Haven Village Suites
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (78)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Private Beach 100 yards from Cottage

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 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, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
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.