
Vacation rentals in Middlebury
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury
Superhost

Apartment in Downtown Stamford
4.83 out of 5 average rating, 6 reviewsSunny 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 favorite

Home in Millerton
4.96 out of 5 average rating, 185 reviewsVacation 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 favorite

Cottage in Norwalk
4.94 out of 5 average rating, 68 reviewsSeaside 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 favorite

Home in New Milford
4.94 out of 5 average rating, 32 reviewsSerene 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 reviewsState Forest Getaway
MattRating, 5 stars1 week 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 favorite

Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviewsSleek and Chic cottage/Pool House
YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favorite

Home in Woodmont
4.98 out of 5 average rating, 43 reviewsBeachfront 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 favorite

Home in Old Saybrook
5 out of 5 average rating, 50 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
ChrisRating, 5 stars4 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.
Destinations to explore
- Hudson Valley Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- The Hamptons Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Boston Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Washington Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Fairfield Beach
- Rye Beach
- Yale University
- Rye Playland Beach
- Catamount Mountain Ski Resort
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Quotonset Beach
- Rye Town Beach
- Giants Neck Beach
- Seaside Beach
- Sunken Meadow State Park
- Woodmont Beach
- Taconic State Park
- Clinton Town Beach
- Jennings Beach
- Thunder Ridge Ski Area
- Rockland Lake State Park
- Marvin Beach
- Walkway Over the Hudson State Historic Park
- Bushnell Park
- Oakland Beach
- Stehli Beach
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes