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

Middlebury Vacation Rentals

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Check prices for these dates

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

Our top choices for Middlebury vacation rentals

Interior

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.
*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.
$369 nightly
The price is $397
Oct 22 - Oct 23
Total with taxes and fees
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.
$691 nightly
The price is $781
Nov 1 - Nov 2
Total with taxes and fees
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
A foggy outdoor scene with trees and a pumpkin on the ground.

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
$238 nightly
The price is $253
Oct 22 - Oct 23
Total with taxes and fees
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
$202 nightly
The price is $226
Oct 23 - Oct 24
Total with taxes and fees
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
$197 nightly
The price is $220
Oct 26 - Oct 27
Total with taxes and fees
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
$331 nightly
The price is $355
Oct 22 - Oct 23
Total with taxes and fees
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
$296 nightly
The price is $316
Oct 22 - Oct 23
Total with taxes and fees
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
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
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
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
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
$319 nightly
The price is $349
Nov 5 - Nov 6
Total with taxes and fees
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
$352 nightly
The price is $384
Oct 22 - Oct 23
Total with taxes and fees
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
$270 nightly
The price is $303
Oct 22 - Oct 23
Total with taxes and fees
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.
$230 nightly
The price is $258
Oct 22 - Oct 23
Total with taxes and fees
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
$316 nightly
The price is $357
Oct 22 - Oct 23
Total with taxes and fees
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.
$286 nightly
The price is $321
Oct 26 - Oct 27
Total with taxes and fees
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.
$319 nightly
The price is $349
Nov 2 - Nov 3
Total with taxes and fees
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.
$314 nightly
The price is $352
Oct 26 - Oct 27
Total with taxes and fees
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.
$173 nightly
The price is $193
Oct 22 - Oct 23
Total with taxes and fees
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
"The cabin was super clean , hot tub was great just make sure to call in ahead of time if you want it set up for a specific time for a fee $35 not bad at all . Really enjoyed my stay will be back soon"
Damian 1-night trip
Posted 1 hour ago
Emrose Luxury Cabins

Find out more about Middlebury

Everything you need to know about Middlebury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlebury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlebury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $66 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlebury rentals

At Expedia, we put the best Middlebury vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Middlebury?

Yes, we offer vacation rentals in Middlebury close to Vermont Folklife Center, or you can select a more remote option if you want a relaxing stay. Our travelers 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 vacation home rentals that Middlebury has to offer?

Water front home with large two tiered deck! 2 bathrooms 😂: Visitors like this Middlebury vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middlebury?

Expedia has 16 vacation 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 vacation rental in Middlebury like?

Vacation rentals are private properties you can stay in for a couple of days or more in Middlebury. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips.