A lakeside scene with a wooden dock, a blue canoe, and a rocky shoreline.

Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Middlebury vacation 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.
$302 nightly
The price is $333
Sep 30 - Oct 1
Total with taxes and fees
*Downtown Middlebury Waterfall Studio Apartment*
A two-story house with a porch, two red doors, and a blue exterior.

2. Downtown Middlebury 3 BR Home - Walk Everywhere!

Downtown Middlebury 3 BR Home - Walk Everywhere!
Middlebury
9.6 out of 10, Exceptional, (34 reviews)
"Great location, very clean"
United States
Karyn M.
$285 nightly
The price is $315
Sep 28 - Sep 29
Total with taxes and fees
Downtown Middlebury 3 BR Home - Walk Everywhere!
A large grassy field with a historic building in the background.

3. 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.
$446 nightly
The price is $483
Oct 26 - Oct 27
Total with taxes and fees
Purple Door Cottage in the heart of Middlebury!
A wooden cabin with a snow-covered roof, surrounded by trees and snow.

4. 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
$293 nightly
The price is $320
Sep 27 - Sep 28
Total with taxes and fees
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.

5. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
$324 nightly
The price is $347
Sep 28 - Sep 29
Total with taxes and fees
Gracious two bedroom just minutes to Middlebury!
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

6. Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, charming, and very clean cabin with excellent communication with team and fun access to trails, hot tub and game room."
United States
Kelly I.
$377 nightly
The price is $412
Oct 25 - Oct 26
Total with taxes and fees
Inviting timber frame cabin in Vermont's Green Mountains
A house with a grey door, two grey Adirondack chairs, and the number 615 on the wall.

7. 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
$224 nightly
The price is $237
Sep 29 - Sep 30
Total with taxes and fees
Charming one bedroom just minutes to Middlebury!
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

8. 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
$370 nightly
The price is $405
Sep 29 - Sep 30
Total with taxes and fees
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has white walls and a blue carpet.

9. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
$318 nightly
The price is $341
Sep 28 - Sep 29
Total with taxes and fees
Tasteful two bedroom just minutes to Middlebury!
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

10. 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.
$395 nightly
The price is $432
Oct 18 - Oct 19
Total with taxes and fees
Cozy and pristine timberframe cabin
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

11. 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, (95 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 18 - Oct 19
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A wooden table with a bottle of wine, glasses, and grapes.

12. 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
$393 nightly
The price is $430
Oct 15 - Oct 16
Total with taxes and fees
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A wooden cabin with a snow-covered roof and a lit entrance.

13. 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
$377 nightly
The price is $412
Oct 25 - Oct 26
Total with taxes and fees
Adorable cabin with screened porch and private fire pit

14. Little City Big Heart

Little City Big Heart
Vergennes
10.0 out of 10, Exceptional, (45 reviews)
"Great house we enjoyed it"
United States
Patsy H.
$401 nightly
The price is $449
Sep 28 - Sep 29
Total with taxes and fees
Little City Big Heart
A wooden interior with large windows, a dining table, chairs, and a sofa.

15. Beautiful timber frame just minutes to Middlebury!

Beautiful timber frame just minutes to Middlebury!
New Haven
10.0 out of 10, Exceptional, (1 review)
"We were 8 people coming to VT to watch our girls play lacrosse at Middlebury. The house is as pictured and perfect for large groups. We really had a great time, it was spacious and perfect for hanging out with a large group. We wished the weather was better so we could use the fire pit. The owner of the property was very easy to deal with and very accommodating. We would all definitely stay here again and recommend a stay at this house. Some of us even said it would be perfect for a small...
United States
Suzanne L.
$852 nightly
The price is $918
Oct 26 - Oct 27
Total with taxes and fees
Beautiful timber frame just minutes to Middlebury!
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

16. 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
$395 nightly
The price is $432
Oct 8 - Oct 9
Total with taxes and fees
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

17. Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views
Ripton
10.0 out of 10, Exceptional, (3 reviews)
"Our cabin was lovely—artfully built, well-stocked, perfectly clean, and very comfortable. We awoke to silence and a beautiful view of the mountains from our screened porch. We are already planning our return!"
United States
Sara S.
$370 nightly
The price is $405
Oct 8 - Oct 9
Total with taxes and fees
Immaculate mountain cabin with awe inspiring sunrise and mountain views
A modern living room with a fireplace, a sofa, a coffee table, and a white door.

18. Beautiful Lake House with whole house renovation & fresh modern appeal!

Beautiful Lake House with whole house renovation & fresh modern appeal!
Crown Point
9.8 out of 10, Exceptional, (13 reviews)
"Awesome place with incredible lake views! The host was very attentive and thoughtful about our needs. I highly recommend!"
United States
Phillip K.
$353 nightly
The price is $399
Sep 27 - Sep 28
Total with taxes and fees
Beautiful Lake House with whole house renovation & fresh modern appeal!
A wooden staircase leading to a dock by a lake surrounded by trees.

19. Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Leicester
10.0 out of 10, Exceptional, (1 review)
"Everything was spectacular! Fern Lake is peaceful and breathtaking. Lake house was wonderful, and amazing. It was spacious, yet homie."
United States
Eric A.
$612 nightly
The price is $685
Sep 28 - Sep 29
Total with taxes and fees
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
A wooden deck with blue chairs and a barbecue grill.

20. 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, (9 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
$204 nightly
The price is $228
Sep 29 - Sep 30
Total with taxes and fees
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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

Brandon Inn

Brandon Inn

10/10 Excellent
"Beautiful"
Jennifer 2-night trip
Posted less than an hour ago
Brandon Inn

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 $170 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 Vermont Folklife Center and UVM Morgan Horse Farm.

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.