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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middlebury vacation rentals

A modern kitchen with a central island, stainless steel appliances, and a large window.

1. 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, (81 reviews)
"Lovely property. Will stay again."
United States
Patricia Y.
The price is ￥62,626
￥118,904 total
includes taxes & fees
Sep 7 - Sep 8
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
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, (33 reviews)
"Great location, very clean"
United States
Karyn M.
The price is ￥30,146
￥68,189 total
includes taxes & fees
Sep 4 - Sep 5
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, (1 review)
"Lovely home in a great location. Very comfortable and we had a great stay"
United States
carol m.
The price is ￥42,448
￥84,075 total
includes taxes & fees
Aug 27 - Aug 28
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
The price is ￥51,591
￥56,234 total
includes taxes & fees
Aug 24 - Aug 25
Robert Frost Mountain Cabins
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

5. 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 ￥51,328
￥68,824 total
includes taxes & fees
Aug 24 - Aug 25
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A house with a grey door, two grey Adirondack chairs, and the number 615 on the wall.

6. 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 ￥17,326
￥42,130 total
includes taxes & fees
Sep 15 - Sep 16
Charming one bedroom just minutes to Middlebury!
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 ￥23,216
￥54,125 total
includes taxes & fees
Aug 24 - Aug 25
Gracious two bedroom just minutes to Middlebury!
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.

8. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is ￥22,696
￥52,296 total
includes taxes & fees
Aug 31 - Sep 1
Tasteful two bedroom just minutes to Middlebury!
A wooden interior with large windows, a dining table, chairs, and a sofa.

9. 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.
The price is ￥99,622
￥181,580 total
includes taxes & fees
Sep 1 - Sep 2
Beautiful timber frame just minutes to Middlebury!
A wooden cabin with a snow-covered roof and a lit entrance.

10. 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 ￥44,461
￥60,626 total
includes taxes & fees
Sep 9 - Sep 10
Adorable cabin with screened porch and private fire pit
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 ￥51,328
￥69,180 total
includes taxes & fees
Sep 8 - Sep 9
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

12. 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.
The price is ￥44,461
￥60,626 total
includes taxes & fees
Sep 9 - Sep 10
Immaculate mountain cabin with awe inspiring sunrise and mountain views
A red barn in a forested area with mountains in the background.

13. 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 ￥34,810
￥44,328 total
includes taxes & fees
Aug 29 - Aug 30
Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

14. 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.
The price is ￥47,895
￥64,904 total
includes taxes & fees
Sep 17 - Sep 18
Inviting timber frame cabin in Vermont's Green Mountains
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 ￥44,461
￥60,626 total
includes taxes & fees
Sep 9 - Sep 10
Cozy and pristine timberframe cabin
A modern kitchen with a central island, built-in appliances, and a dining area with a view.

16. 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 ￥28,495
￥62,455 total
includes taxes & fees
Aug 24 - Aug 25
Bridges Resort
A wooden table with a bottle of wine, glasses, and grapes.

17. 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 ￥47,895
￥64,548 total
includes taxes & fees
Sep 13 - Sep 14
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

18. 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, (88 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 ￥19,630
￥31,244 total
includes taxes & fees
Aug 27 - Aug 28
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A wooden deck with blue chairs and a barbecue grill.

19. 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 ￥14,147
￥36,495 total
includes taxes & fees
Aug 26 - Aug 27
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A modern living room with a fireplace, a sofa, a coffee table, and a white door.

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

Beautiful Lake House with whole house renovation & fresh modern appeal!
Crown Point
10.0 out of 10, Exceptional, (12 reviews)
"Awesome place with incredible lake views! The host was very attentive and thoughtful about our needs. I highly recommend!"
United States
Phillip K.
The price is ￥42,773
￥63,421 total
includes taxes & fees
Aug 26 - Aug 27
Beautiful Lake House with whole house renovation & fresh modern appeal!
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

Circle Court Motel

Circle Court Motel

8/10 Good
"Clean room but tight. Very small bathroom, tight shower stall. Beds comfortable, air conditioning worked well. We would stay again."
Mary 2-night trip
Posted 2 hours ago
Circle Court Motel

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:

  • View our selection of featured holiday rentals in Middlebury
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Look no further and take a look at our great range of rental properties in Middlebury!

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?

Breathtaking views from charming lakefront home on beautiful Lake George: You might want to consider this vacation home rental near Middlebury, which is located on a lake and has a patio, a barbecue grill, 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 you can cook with friends or family.

How many vacation rentals are there in Middlebury?

Expedia has 14 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.