A wooden pier extending into a lake, surrounded by lush greenery and a prominent lighthouse on a small island.

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middlebury holiday rentals

A historic town with a river, buildings with traditional architecture, and a waterfall.

1. *Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
9.6 out of 10, Exceptional, (11 reviews)
"This is the first review I have ever written. The property and the ownership were fantastic. I found the property to be better than advertised and can’t wait to stay there again. Highly recommended! "
United States
Steve S.
The price is AU$468
includes taxes & fees
26 Oct - 27 Oct
*Downtown Middlebury Waterfall Studio Apartment*
A large grassy field with a historic building in the background.

2. Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
9.4 out of 10, Exceptional, (3 reviews)
"Lovely home in a great location. Very comfortable and we had a great stay"
United States
carol m.
The price is AU$558
includes taxes & fees
22 Oct - 23 Oct
Purple Door Cottage in the heart of Middlebury!
A modern kitchen with a central island, stainless steel appliances, and a large window.

3. 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, (85 reviews)
"A perfect spot for our Middlebury reunion gathering - with great living/gathering space indoors and outdoors. The home is comfortable, clean, convenient, with really nice cozy touches. Thank you!"
United States
Page E.
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
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$360
includes taxes & fees
22 Oct - 23 Oct
Charming one bedroom just minutes to Middlebury!
A wooden deck with blue chairs and a barbecue grill.

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

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is AU$328
includes taxes & fees
22 Oct - 23 Oct
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

6. 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, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is AU$319
includes taxes & fees
26 Oct - 27 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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$506
includes taxes & fees
22 Oct - 23 Oct
Gracious two bedroom just minutes to Middlebury!
A covered outdoor seating area with two chairs and a table, a no-smoking sign, and a view of trees and sky.

8. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is AU$467
includes taxes & fees
16 Nov - 17 Nov
Tasteful two bedroom just minutes to Middlebury!
A wooden table with a bottle of wine, glasses, and grapes.

9. 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, (13 reviews)
"It is a beautiful location in a fully equipped cabin off the beaten path."
United States
Steven
The price is AU$489
includes taxes & fees
4 Nov - 5 Nov
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

10. 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$489
includes taxes & fees
4 Nov - 5 Nov
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

11. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is AU$491
includes taxes & fees
5 Nov - 6 Nov
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
A wooden cabin with a snow-covered roof, surrounded by trees and snow.

12. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (43 reviews)
"Very nice place great owner"
United States
Joe
The price is AU$545
includes taxes & fees
22 Oct - 23 Oct
Robert Frost Mountain Cabins
A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

13. 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$430
includes taxes & fees
22 Oct - 23 Oct
Ski-in/ski-out condo with mountain view, seasonal pool
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

14. 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$366
includes taxes & fees
22 Oct - 23 Oct
Ski-in/ski-out condo near the slopes with pool, fast WiFi & garden-level patio
A modern living room with a sofa, a small round table, and a kitchen in the background.

15. Lake Days, Trails & More! Updated Apt in Mineville

Lake Days, Trails & More! Updated Apt in Mineville
3.0 star property
Moriah
The price is AU$511
includes taxes & fees
22 Oct - 23 Oct
Lake Days, Trails & More! Updated Apt in Mineville
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, (20 reviews)
"Great location and amenities. "
United States
Scott H.
The price is AU$448
includes taxes & fees
1 Nov - 2 Nov
Mountain-view condo with fireplace, 3 pools, tennis & gym - near skiing
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

17. 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$489
includes taxes & fees
4 Nov - 5 Nov
Cozy and pristine timberframe cabin
A wooden deck with a view of a forested mountain range.

18. 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$492
includes taxes & fees
1 Nov - 2 Nov
Welcoming Condo with Shared Pools, Easy Access to Golf & Slopes
An outdoor seating area with Adirondack chairs, a stone fire pit, and a picnic table.

19. Lovely condo near skiing with 3 pools, sauna, fitness room & balcony

Lovely condo near skiing with 3 pools, sauna, fitness room & balcony
Warren
6.8 out of 10, (3 reviews)
"Very cozy and perfect! We enjoyed the stay for the night. We weren’t able to use the facilities but the accommodation was very comfortable, seating and bed. I could hear a stream below in the woods and was nice from the porch. There is an apartment above, so you can hear walking but in was totally fine. The pool, grills and tennis right across the parking. It was very wooded and up in the mountains so the fans and windows were perfect. We would definitely go back!"
United States
katherine l.
The price is AU$278
includes taxes & fees
22 Oct - 23 Oct
Lovely condo near skiing with 3 pools, sauna, fitness room & balcony
A room with a large window overlooking a forest in autumn.

20. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (51 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
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
"Such great atmosphere, thank you so much for making my birthday so wonderful"
Dorjana 2-night trip
Posted 3 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$97 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?

Water front home with large two tiered deck! 2 bathrooms 😂: This holiday home rental outside of Middlebury is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Town Hall Theater and Henry Sheldon Museum of Vermont History, whereas Green Mountain National Forest and Cornwall Swamp Wildlife Management Area are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include UVM Morgan Horse Farm and Vermont Folklife Center.

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.