Vacation rentals in Middlebury

4.96 out of 5 average rating, 103 reviews

Chalet in Jay

Doe - A- Deer

BradleyRating, 5 stars2 months ago

Doe-A-Deer was absolutely beautiful, we had a group of 11 that visited for our yearly ski trip for an extended weekend. The house was peaceful, clean, and modern. Only 20 minutes from whiteface mountain. Nice amenities and we loved the fireplace! Would love to stay here again, thanks again!

5 out of 5 average rating, 5 reviews

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

SeanRating, 5 stars2 months ago

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

4.98 out of 5 average rating, 61 reviews

Townhouse in Stowe

Stowe Depot townhouse - Fireplace -Deck- Rec Path

PaulRating, 5 stars2 months ago

This 2 story townhouse in Stowe Village was the perfect home base for our visit, offering both comfort and convenience. Located just steps from shops and restaurants, we loved being able to explore the charming village without needing to drive. The townhouse itself has a well-equipped kitchen that made meal preparation a breeze, along with a spacious dining and living area that provided plenty of room. The layout was ideal for gathering, whether enjoying a home-cooked meal or simply unwinding in the cozy living space. Communicating with Kim was very easy and she was super to work with. The home has comfortable mattresses & bedding ensuring restful nights. The townhouse was clean, well-maintained, and stocked with everything we needed. The combination of its prime location, welcoming ambiance, and thoughtful amenities made for a truly enjoyable experience. We highly recommend this townhouse to anyone visiting Stowe VT.

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

Apartment in Waterbury Center

4.98 out of 5 average rating, 63 reviews

Sir Richards Waterbury Stowe 2 B Lake View Escape

TarynnRating, 5 stars3 months ago

Barbara was a wonderful host. The space was perfect for the four of us over the holiday break. Our kids especially enjoyed the game room and took advantage of the puzzles. Cozy home with great views and privacy.

4.96 out of 5 average rating, 224 reviews

Home in Addison

Brthtkng New Premier Lake Champlain Wfrnt Escape!

RobertRating, 5 stars2 days ago

A perfect spot for us and our small pooch. The only challenge was that I had to carry our small dog upstairs, because she couldn’t do the stairs. Wonderful,private location, and Barb dealt with an internet issue very promptly, but also respected our privacy.

5 out of 5 average rating, 4 reviews

Condo in Pomfret

Next to Saskadena Ski, Great Views | Half Past Six

AutumnRating, 5 stars2 months ago

Family of five on a northeast road trip enjoyed a rather cold but very beautiful snowy few days in this home that clearly has been loved by many for many, many years. We enjoyed being a part of the history. Kids had fun in the snow exploring the backyard. Plenty of space and beautiful views. Only downside was not being able to use the fireplaces!

4.95 out of 5 average rating, 175 reviews

Cabin in Jay

Green Valley Lodge- restful retreat

LisaRating, 5 stars1 month ago

This was our second year staying at Carlos’ place for our family ski vacation. It’s so cozy and has plenty of room for my sons’ growing families. Everything is labeled with easy instructions…no need to flip through a manual. The kitchen is a dream and is stocked with every kind of pot, pan, baking dish, utensil or appliance you would need. Carlos was super helpful and accommodating! We’re planning on including Carlos’ place as part of our annual family tradition!

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What guests are saying

Lovely 1 bedroom

4.97 out of 5 average rating, 67 reviews6 months ago

Highly recommended space and host! Kurt is hands down an A+ super host! We arrived in Burlington in the evening with having another Airbnb reservation that we found not to be a good fit for us! Frantically searching for other Airbnb accommodations for the night, several hosts had availability but showed no urgency to help us. Kurt literally stopped what he was doing to go and turn lights and heat on for us. He also left water, a couple beers, and creamer in the fridge for our morning coffee, which too was provided. The space is exactly how it was pictured. Clean, uncluttered, and beautiful! Kurt’s place has great location in a charming quiet neighborhood with driveway parking. Comfortable bed and great water pressure in the shower was also great to have! Finding this place last minute was the cherry on top of our amazing Burlington experience….and we will be back! Thanks again

Apartment in Burlington

What guests are saying

4 Bedroom Lake House Lake George Views and Beach

4.6 out of 5 average rating, 10 reviews2 months ago

Spent our Annual President's Day weekend at the Lake House and it was perfect for a relaxed and peaceful getaway. Had everything you'd need for a weekend away in the mountains. From start to finish the process was seamless. The hosts were friendly and helpful and the house was clean and cozy with views of Lake George and surrounding mountains. Interested in staying in the warmer months as the location is right on the lake! Would highly recommend.

Home in Lake George

What guests are saying

Breathtaking, waterfront rental on Lake Champlain

4.92 out of 5 average rating, 25 reviews6 months ago

Convenient to our hunting spot, the accomodations were closer and far more comfortable than where we have stayed in the past. Ardie very accommodating, and helpful during our stay. Two of us will be returning in two weeks and hopefully again next year.

Cottage in Shoreham

What guests are saying

The Bumble Bear Inn, Bolton Ldg

4.88 out of 5 average rating, 26 reviews2 months ago

This is our second annual visit to the Bumble Bear Inn. We love all the TVs and WiFi but especially the game room! Kitchen is well-stocked and morning coffee in the sunroom is very relaxing. Great place to visit in the winter! Kim and Cameron are very responsive and great!

Home in Bolton

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Stay near Middlebury's top sights

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Other great vacation rentals in Middlebury

5 out of 5 average rating, 20 reviews

Home in Richmond

Sunset Treehouse

JustinRating, 5 stars1 month ago

If you’re looking to ski at Bolton Valley, really tough to beat this location unless you’re right in the resort. Worked out very conveniently for our family of 4 (2 adults and 2 young kids). Cleanliness is important to us and the bathroom, kitchen, foyer, etc. we’re all in great shape and updated. King size bed was comfortable. Some of the bedroom furniture was a bit dated, but was livable given the rest of the nice amenities and overall cleanliness of the apt….and the location to the lifts… Lucas was very upfront about the fact that we would need to bring an air mattress of some sort for the kids. This worked out more than fine as we sat up the mattress in the living room. All in all, this apt would work out well for anyone wanting close proximity to the ski lifts…

4.96 out of 5 average rating, 94 reviews

Cottage in Lewis

A slice of Heaven

ChrisRating, 5 stars3 months ago

We had a fantastic stay at in this remote getaway in the Adirondacks. The property was perfect for us and our dog, which plenty of space to explore and a cozy fireplace to come back to. The drive to Lake Placid is easy and scenic, and the host's recommendations for local spots were great. The host was also very personable and even stopped by to drop off cookies. Overall, a perfect retreat!

4.75 out of 5 average rating, 92 reviews

Condo in Killington

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago

Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

Guesthouse in Lake George

4.73 out of 5 average rating, 22 reviews

Whitetail Deer Cabin #16 at the Adirondack Lodge

JanisRating, 5 stars7 months ago

Beautiful cabin with authentic Adirondack furniture in great location!

4.8 out of 5 average rating, 15 reviews

Cabin in Barnard

Private post & beam log cabin on Macintosh Pond.

NinaRating, 5 stars3 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

4.82 out of 5 average rating, 45 reviews

Villa in Stowe

Beautiful 5 Bedroom Villa with Amazing Views

RichardRating, 5 stars3 months ago

Very nice home with great amenities. Great location to and from everything. Nicely distributed with space for everyone. Beds were comfortable and the home has plenty of towels etc. Overall it was a great place for weekend or longer. Maria was easy to communicate with and there were no issues.

5 out of 5 average rating, 8 reviews

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago

I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!