Middlebury Holiday Rentals

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Holiday Rentals in Middlebury

Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (264)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
United States
Melissa Anne R.
Cozy Loft for two with Hot Tub & Mtn Views
Bridges Resort
3.5 star property
8.2 out of 10, Very good, (15)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
The price is AU$313
includes taxes & fees
26 Oct - 27 Oct
Bridges Resort
Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is AU$239
includes taxes & fees
20 Oct - 21 Oct
Trout House Village Resort
Ultimate relaxing vacation
9.8 out of 10, Exceptional, (207)
"The cottage was so cozy and comfy."
United States
Barsha
The price is AU$279
includes taxes & fees
22 Oct - 23 Oct
Ultimate relaxing vacation
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (518)
"Great location. Very cute cabin and it had everything you would need even plenty of wood for the fire pit. We will be staying at one of Jeff’s places again soon no doubt."
United States
Bryan C.
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Lake George Water Front Cabin Spectacular Views
9.6 out of 10, Exceptional, (35)
"The house was perfect for my family! The teens loved kayaking! The view was absolutely stunning! Wish we could have stayed longer! Will stay again next year!"
United States
Jillian B.
The price is AU$1,667
includes taxes & fees
20 Oct - 21 Oct
Lake George Water Front Cabin Spectacular Views
Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi
The price is AU$460
includes taxes & fees
20 Oct - 21 Oct
Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi
Killington Vermont Ski and Snowmobiling House
9.2 out of 10, Wonderful, (44)
"Spacious and nice location. The home met our needs. Basic home with some necessities lacking like soap, shampoo, washcloths, and paper towels. Coffee maker did not function well. Cooking utensils could use an upgrade. Needs a thorough cleaning and we noticed this right away upon arrival. Hot tub did not seem to work. No air conditioning, which should be clearly noted in the property description."
United States
Jon D.
Killington Vermont Ski and Snowmobiling House
A Canopy under the Stars
10.0 out of 10, Exceptional, (1)
"Absolutely stunning spot, the first night we were a little worried about the canopy being very open with the front not zipping shut and the bottom being open all around but we had no issues whatsoever not even a worry. Totally awesome all around!"
United States
Emilia T.
The price is AU$201
includes taxes & fees
20 Oct - 21 Oct
A Canopy under the Stars
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
9.2 out of 10, Wonderful, (12)
"We loved this house, the layout and location is great! Well equipped, clean and nicely decorated. Plenty of room for all 8 of us."
United States
Donna N.
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
Charming cabin located one minute from the base of Sugarbush Resort
9.2 out of 10, Wonderful, (25)
"My friend and I had a great time. It is a tiny place, but it is cozy with everything you could need or ask for. Colin is very responsive. Absolutely will stay again!"
United States
Zackary G.
Charming cabin located one minute from the base of Sugarbush Resort
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (157)
"Close to everything - downtown Warren/Waitsfield, swimming, and biking trails. Perfect space for the weekend. "
United States
Elizabeth B.
The price is AU$685
includes taxes & fees
26 Oct - 27 Oct
Stetson Hollow Cabin by Stetson Brook
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
10.0 out of 10, Exceptional, (190)
"Beautiful area excellent vacation "
United States
David B.
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
Glamping hut with WiFi in Ripton, biking, hiking, skiing
10.0 out of 10, Exceptional, (1)
"Super cute and cozy! It was perfect."
United States
Sarah D.
The price is AU$260
includes taxes & fees
26 Oct - 27 Oct
Glamping hut with WiFi in Ripton, biking, hiking, skiing
BEAUTIFUL SECLUDED RUSTIC camp site. Waterfall, creek, swimming hole & trails.
8.0 out of 10, Very good, (5)
"We had a wonderful stay. The property was just as advertised and the hosts provided clear instructions and directions about getting there, where to park, accessing the camp site, etc. We stayed on the overlook site, which had a raised wood platform for the tent and was warmer at night for camping in cold temperatures. Was fun to explore the swimming hole and nearby trails."
United States
Shannon A.
The price is AU$99
includes taxes & fees
20 Oct - 21 Oct
BEAUTIFUL SECLUDED RUSTIC camp site. Waterfall, creek, swimming hole & trails.
Water front home with large two tiered deck! 2 bathrooms 😂
9.4 out of 10, Exceptional, (105)
"My family enjoyed their stay very much. "
United States
Miriam N.
Water front home with large two tiered deck! 2 bathrooms 😂
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
8.4 out of 10, Very good, (18)
"The spectacular views from the back porch were amazing. We were in the area for a retirement party so we did not spend as much time at the house as we would have like to. "
United States
Kristin v.
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
Lake George Waterfront Paradise Dock Slip
10.0 out of 10, Exceptional, (3)
"Beautiful house, amazing stay, great views! We enjoyed it!"
United States
Dawid R.
Lake George Waterfront Paradise Dock Slip
Classic Vermont Farmhouse near Sugarbush Resort
9.6 out of 10, Exceptional, (43)
"Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!"
United States
Nathalie B.
Classic Vermont Farmhouse near Sugarbush Resort
Lovely cabin nestled in the woods one minute from Sugarbush Resort
9.8 out of 10, Exceptional, (20)
"Great dog freindly cabin. Love the hot tub! Just as good as the first time,"
United States
Jack G.
Lovely cabin nestled in the woods one minute from Sugarbush Resort
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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Top Middlebury Hotel Reviews

Find out more about Middlebury

Everything you need to know about Middlebury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middlebury holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury holiday rentals we have selected for you start as low as AU$99 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Danforth Pewter, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.

What are some of the best holiday rentals that Middlebury has to offer?

Beatiful Custom Log Home " Bear Lodge": This holiday home rental outside of Middlebury is located on a lake, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Middlebury?

Expedia has 13 holiday rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include National Museum of the Morgan Horse and Holy Cow Inc., whereas Green Mountain National Forest and Middlebury Dog Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Pulp Mill Covered Bridge and Otter Creek Brewing.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.