Holiday houses in Middlebury

Find and book unique accommodation on Airbnb

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Popular amenities for Middlebury holiday rentals

Stay near Middlebury's top sights

Quassy Amusement Park & Waterpark39 locals recommend
Hop Brook Lake10 locals recommend
Mill House Antiques3 locals recommend
Dunkin'7 locals recommend
Vyne Restaurant & Bar5 locals recommend
Waterbury Hospital5 locals recommend

Other great holiday rentals in Middlebury

Superhost
Apartment in Downtown Stamford
4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars4 months ago
Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit
Top Guest favourite
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars2 weeks ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Top Guest favourite
Home in Millerton
4.96 out of 5 average rating, 185 reviews

Vacation Home In Millerton

BettyRating, 5 stars2 weeks ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favourite
Cottage in Norwalk
4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars2 weeks ago
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!
Guest favourite
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Superhost
Home in Cornwall
4.83 out of 5 average rating, 98 reviews

State Forest Getaway

MattRating, 5 stars5 days ago
Such a gracious host, easy and everything was flawless. The space is just magical, so relaxing, and the surrounding areas are beautiful. Feels like home from the minute you walk in.
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top Guest favourite
Home in Old Saybrook
5 out of 5 average rating, 50 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

ChrisRating, 5 stars2 days ago
My family and I enjoyed our stay. The accommodation was well appointed with all ameneties and cooking utilities to provide for a wonderful stay. We enjoyed the private back yard area and porch for dinners outside. Harvey's Beach is a walkable and we enjoyed some beach time there. Irina is a very responsive host and provided some great local tips on restaruants and places to visit. We would recommend this spot for folks looking for a location both close to beaches and town area. The accommodation is welcoming and very suitable for families or groups.

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