Holiday rentals with outdoor seating in Middlebury

We had an amazing stay at Bjorn's beautiful home where it was as picture-perfect as advertised! It is a gorgeous and modern home that was clean, well-stocked, and uniquely designed in such stunning surroundings (even in the rainy weather!). We cannot recommend Bjorn's home enough and are so appreciative of his accommodations in helping us celebrate our Middlebury grad!

We had a lovely stay at the Looking Glass. It’s a special place - a great launch pad if you’re in VT for the gravel biking and a restorative peaceful place to return to after a long ride. Thank you, Angela!

In a word: Wow! This is a dream home in just the perfect location. Whether you love Lake Dunmore, or are visiting for the first time, you will simply adore this lovely lakefront home. Beyond comfortable, immaculate, and oh-so charming. How wonderful to wake up and go for a swim or a paddle on the lake. Maureen is an exemplary host! We wish we could’ve stayed longer, and will definitely be back.

That was a peaceful vacation with my family. First and foremost, the house was spotless clean. There were plenty of toys for my six-year-old niece to enjoy. Kevin had a keen eye for detail, and we had everything guests needed for a comfortable stay. The lake was also a highlight of the trip. We went canoeing, and it was a truly enjoyable experience in that picturesque setting. I hope we can return soon.

We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

We really enjoyed our stay! Lots of space and amenities! Great for families. Large beautiful well equipped kitchen with a lot of seating. Attached living space was very comfortable. Washer and dryer with ironing board and iron. Hair dryer and curling iron! Would definitely stay again when in the area. <3

This place is a gem! The location is fantastic – a beautiful, peaceful home right by the river. If you enjoy fishing, the trout are plentiful - we spent several days catching and releasing. The gardens and ponds were stunning. Philip is a terrific host, and the town of Brandon is lovely and just a short drive away. We had everything we needed, whether we wanted to cook in the modern kitchen or eat out at a nice restaurant. It’s the perfect mix of rustic and comfortable. The neighboring garage rental wasn't an issue at all. Highly recommend!

This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!

Audrey’s Porcupine Farm Barn was the perfect place for us and our pup to get some respite from our day to day grind. With scenic vistas outside our window the space was an ideal blend of rustic and comfortable, and Audrey was around to answer any questions and assist us whenever we needed. We would absolutely stay again - and hopefully will soon!

For the price, this is the perfect spot for a little weekend getaway. The restaurants and surrounding areas are inexpensive and good quality. I would recommend this spot to anyone looking to get away from the city and into nature!

Loved staying with Sandra and Jason! They are great hosts and did a great job on the Airbnb. We knew there were going to be mosquitoes, but we didn’t know that there were going to be so many, I would advise bringing bug spray. They let us use their kayaks which was an awesome experience. 10/10 would stay again.

Amy’s place offered us a wonderful, relaxing stay at Monkton, with its stunning view of the mountains and peaceful surroundings. The clean, nicely furnished apartment was lovely and cozy. Amy was a great host. She was warm, welcoming, and very accommodating. Thank You Amy for the delicious apple cake chunks.

We had a great holiday weekend in Charlotte at Robert's apartment. It was close to the mountains we wanted to climb and a nature preserve where we skied. Close to Burlington and Middlebury where we found dinner each night. The apartment is cozy and comfortable; really a delightful place. We also met Robert who was funny and the perfect host. We stayed during a massive winter storm that dumped so much snow on the area and Robert was always very interested in making sure we could get out of the driveway! There were also thoughtful snacks and what not for us when we arrived which is such a nice bonus. We will definitely check to see if the apartment is available the next time we come to VT. Thank you so much, Robert! We hope to stay with you again soon.

Kelly’s place has been a great place to stay in Bristol while in town for a multi-week project. Easy to find and convenient, yet private as well. Love that the stackable laundry unit is available, so helpful! Thank you again for the great pet-friendly accommodations!!

Definitely stay here! ALL the reviews are spot on. Close to everything so you can walk or easy Uber ride. Off street parking is huge! The bed is super comfortable. It's bigger and cheaper than a hotel in the area. The bike trail is close. Waterfront Park is close. It is so convenient yet quiet. The neighbors are met were super friendly. The kitchen is stocked with everything you might need. Coffee, eggs treats, pasta etc etc !! A huge snack basket. Bathroom supplies!! We wished we were able to stay another night. It's as nice and nicer than the pics. Really plenty of room for two people for a night/weekend/week stay! If you need more space, Abbott has others in the same area. Not a question , stay at one of his places! I can't say enough. I know the area and have family there, but Abbott is great with suggestions or questions. Oh.. he has multiple phone chargers there. We forgot ours. I am not doing it justice! Stay and find out for yourself like we did! A+++

Had a great stay! Brought the split boards and enjoyed the property. Jon and Cathy take great care of the entire property making sure it is accessible even during a snowstorm. It was the perfect Vermont get away. We can’t wait to go back!

This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

Couldn’t have asked for more. Cozy, clean and such a comfortable place to stay and exactly what was described in the listing. I’ll certainly be booking again! Tricia’s communication was perfect, everything very clear and didn’t have to reach out with extra questions.

Great place to stay. Beautiful walking trails and very peaceful in the off season. Enjoyed the over the mountain ride into Stowe each morning.

I just want to say I was very pleased about the rapid response I had gotten from him. The place was clean and relaxing like home . I will back next time I visit Vermont ! Kim.

Our entire group thoroughly enjoyed our stay at this beautiful home! The place is exactly as listed but even more stunning in person. We felt right at home! It is clear Josh has thought of everything. All of the little touches and amenities are well thought out. We easily fit our group of 9, with plenty of space for everyone to hang out and relax. Josh was a great host and very friendly and easy to communicate with. I would certainly rent this space again and recommend it to anyone looking for a relaxing getaway to Stowe!

We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

⭐️⭐️⭐️⭐️⭐️ Perfect Father–Son Getaway at CozyCub! My son and I stayed one night at the CozyCub condo in Killington, and once again, Dan and Holly delivered a flawless experience. From the moment we arrived, everything was spotless, cozy, and thoughtfully arranged—exactly what we look for in a mountain bike trip base. Comfort & Cleanliness: The condo was pristine, with comfy beds and fresh linens—like a home away from home. Attention to Detail: Every essential was readily available, from kitchen basics to crisp towels. Perfect for a Duo: Ideal layout and amenities for just the two of us—no waste, just well-tailored space. Consistent Excellence: We’ve stayed with Dan and Holly before, and CozyCub continues to meet our high expectations. This stay earned a full five stars. Thanks again to Dan and Holly for providing the perfect retreat—we’ll be back for our next biking adventure together!

Very comfortable stay - convenient to ski wither Sugarbush or Mad River. Philip sent specific instructions for turning the heat up on arrival. It took a little while to warm up, but individual thermostats in LR and BR worked nicely. Local recommendations for restaurants and such were spot on.