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Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middlebury holiday rentals

A large grassy field with a historic building in the background.

1. Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
10.0 out of 10, Exceptional, (2 reviews)
"Lovely home in a great location. Very comfortable and we had a great stay"
United States
carol m.
The price is AU$741
includes taxes & fees
6 Sept - 7 Sept
Purple Door Cottage in the heart of Middlebury!
A modern kitchen with a central island, stainless steel appliances, and a large window.

2. Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
Middlebury
10.0 out of 10, Exceptional, (82 reviews)
"Lovely property. Will stay again."
United States
Patricia Y.
The price is AU$1,046
includes taxes & fees
4 Oct - 5 Oct
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
A wooden deck with blue chairs and a barbecue grill.

3. Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is AU$322
includes taxes & fees
7 Sept - 8 Sept
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A house with a grey door, two grey Adirondack chairs, and the number 615 on the wall.

4. Charming one bedroom just minutes to Middlebury!

Charming one bedroom just minutes to Middlebury!
New Haven
10.0 out of 10, Exceptional, (2 reviews)
"Lovely unit, clean, well equipped, quiet location"
United States
Jane
The price is AU$339
includes taxes & fees
16 Sept - 17 Sept
Charming one bedroom just minutes to Middlebury!
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

5. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (89 reviews)
"Definitely super SUPER clean all throughout! The ambiance is perfect, just a beautiful cottage with all the amenities you might need. Perfect place to stay."
United States
Julian V.
The price is AU$265
includes taxes & fees
10 Sept - 11 Sept
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A wooden cabin with a snow-covered roof, surrounded by trees and snow.

6. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place great owner"
United States
Joe
The price is AU$545
includes taxes & fees
8 Sept - 9 Sept
Robert Frost Mountain Cabins
A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a living room with a sofa.

7. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is AU$527
includes taxes & fees
16 Sept - 17 Sept
Gracious two bedroom just minutes to Middlebury!
A red barn in a forested area with mountains in the background.

8. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
Ripton
9.8 out of 10, Exceptional, (6 reviews)
"The property was very generously provisioned, pet friendly, clean and comfortable."
United States
Lani C.
The price is AU$341
includes taxes & fees
10 Sept - 11 Sept
Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
A bedroom with a bed, bedside table, lamp, dresser, mirror, and a window with curtains.

9. Four Season Condo: seasonal pool, ski, hike & golf

Four Season Condo: seasonal pool, ski, hike & golf
Warren
The price is AU$352
includes taxes & fees
6 Sept - 7 Sept
Four Season Condo: seasonal pool, ski, hike & golf
A spacious room with a large window, a beige sofa, a wooden dining table, and a small coffee table.

10. Four Season Condo: seasonal pool, close to Sugarbush, golf & hiking

Four Season Condo: seasonal pool, close to Sugarbush, golf & hiking
Warren
The price is AU$315
includes taxes & fees
7 Sept - 8 Sept
Four Season Condo: seasonal pool, close to Sugarbush, golf & hiking
A wooden cabin with a snow-covered roof and a lit entrance.

11. Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is AU$519
includes taxes & fees
9 Sept - 10 Sept
Adorable cabin with screened porch and private fire pit
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

12. Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio

Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
Warren
9.4 out of 10, Exceptional, (23 reviews)
"Enjoyable stay"
United States
Eric W.
The price is AU$357
includes taxes & fees
14 Sept - 15 Sept
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
A wooden deck with a view of a forested mountain range.

13. Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes

Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes
Warren
9.4 out of 10, Exceptional, (38 reviews)
"Nice view - Well-stocked kitchen - Nice pool and tennis courts "
United States
Michael L.
The price is AU$487
includes taxes & fees
12 Sept - 13 Sept
Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes
A wooden table with a bottle of wine, glasses, and grapes.

14. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is AU$553
includes taxes & fees
13 Sept - 14 Sept
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

15. Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is AU$519
includes taxes & fees
9 Sept - 10 Sept
Cozy and pristine timberframe cabin
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and trees.

16. Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing

Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing
Warren
8.8 out of 10, Excellent, (18 reviews)
"Great location and amenities. "
United States
Scott H.
The price is AU$443
includes taxes & fees
11 Sept - 12 Sept
Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing
A modern kitchen with a central island, built-in appliances, and a dining area with a view.

17. Bridges Resort

Bridges Resort
2.0 star property
Warren
8.2 out of 10, Very good, (30 reviews)
"close to the mountain"
United States
Brian Shultis
The price is AU$545
includes taxes & fees
9 Sept - 10 Sept
Bridges Resort
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

18. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is AU$589
includes taxes & fees
16 Sept - 17 Sept
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

19. Ski-in/ski-out condo with mountain view, seasonal pool

Ski-in/ski-out condo with mountain view, seasonal pool
Warren
The price is AU$421
includes taxes & fees
8 Sept - 9 Sept
Ski-in/ski-out condo with mountain view, seasonal pool
A modern kitchen with wooden beams, a dining area with a table and chairs, and large windows offering a view of the forest.

20. Magnificent any time of year

Magnificent any time of year
East Warren
10.0 out of 10, Exceptional, (49 reviews)
"The location was perfect for attending a wedding at Sugarbush."
United States
Sheila
The price is AU$509
includes taxes & fees
8 Sept - 9 Sept
Magnificent any time of year
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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"Here is our review of the stay and the cabin , Prior to arrival we got a message from the hotel on Expedia to give us the information needed for the check in . It was clear and very simple and easy to understand . When we entered the cabin we were very happy with how clean the cabin was and how well thought out the space was . For a small cabin it has everything you may need , refrigerator , microwave, stove top , pot and a pan , salt and pepper , utensils , plates , cups , wine opener , tea kettle , bowls , kitchen sink . Bathroom shower had very good water pressure and the water got warm really fast . The cabin comes with a wall mounted heating/ cooling unit . Outside we loved the hot tub and the fire pit was very relaxing . We are looking forward to returning soon ."
Jackie 1-night trip
Posted 12 hours ago
Emrose Luxury Cabins

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$240 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 Vermont Folklife Center, 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?

Breathtaking views from charming lakefront home on beautiful Lake George: This holiday home rental outside of Middlebury is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middlebury?

Expedia has 16 holiday rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include Henry Sheldon Museum of Vermont History and Kevin P. Mahaney '84 Center for the Arts, whereas Green Mountain National Forest and Middlebury Falls are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Vermont Folklife Center and UVM Morgan Horse Farm.

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.