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Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middlebury vacation 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
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 CA $247
CA $551 total
includes taxes & fees
Nov 16 - Nov 17
Purple Door Cottage in the heart of Middlebury!
A modern kitchen with white cabinets, a coffee machine, and a wooden accent wall.

2. 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 CA $118
CA $311 total
includes taxes & fees
Nov 15 - Nov 16
Charming one bedroom just minutes to Middlebury!
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

3. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is CA $174
CA $420 total
includes taxes & fees
Nov 16 - Nov 17
Tasteful two bedroom just minutes to Middlebury!
A snow-covered house with a lit entrance and a small outdoor light feature.

4. 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 CA $127
CA $308 total
includes taxes & fees
Nov 14 - Nov 15
Glamping hut with WiFi in Ripton, biking, hiking, skiing
A modern kitchen with stainless steel appliances, a granite countertop, and pendant lighting.

5. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is CA $211
CA $465 total
includes taxes & fees
Nov 16 - Nov 17
Gracious two bedroom just minutes to Middlebury!
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 CA $183
CA $272 total
includes taxes & fees
Nov 19 - Nov 20
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A lakeside view with a fire pit and chairs, surrounded by mountains and trees.

7. Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (82 reviews)
"Awesome place. We will be back!"
United States
Christopher T.
The price is CA $228
CA $318 total
includes taxes & fees
Nov 16 - Nov 17
Doc's Lake house 1st floor, 2 bedroom apartment
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

8. 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 CA $368
CA $480 total
includes taxes & fees
Nov 19 - Nov 20
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
A red barn in a forested area with mountains in the background.

9. 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, (7 reviews)
"The property was very generously provisioned, pet friendly, clean and comfortable."
United States
Lani C.
The price is CA $326
CA $397 total
includes taxes & fees
Nov 28 - Nov 29
Charming Barn Carriage House in Green Mountains of Vermont Near 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.
The price is CA $368
CA $480 total
includes taxes & fees
Nov 19 - Nov 20
Cozy and pristine timberframe cabin
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

11. 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 CA $368
CA $480 total
includes taxes & fees
Nov 18 - Nov 19
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
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
The price is CA $368
CA $480 total
includes taxes & fees
Nov 18 - Nov 19
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A modern kitchen with white cabinets, a stainless steel refrigerator, and a bar area with stools.

13. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio
Warren
9.0 out of 10, Wonderful, (24 reviews)
"Enjoyable stay"
United States
Eric W.
The price is CA $82
CA $370 total
includes taxes & fees
Nov 14 - Nov 15
Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio
A living room with a fireplace, a television mounted on the wall, and a balcony with outdoor furniture.

14. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

Out to Lunch trail ski-in/ski-out condo with balcony and heated pool
Warren
The price is CA $133
CA $451 total
includes taxes & fees
Nov 14 - Nov 15
Out to Lunch trail ski-in/ski-out condo with balcony and heated pool
A rustic cabin surrounded by autumn foliage.

15. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.2 out of 10, Wonderful, (13 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
The price is CA $77
CA $354 total
includes taxes & fees
Nov 18 - Nov 19
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

16. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (28 reviews)
"We had a great time! "
United States
Allie T.
The price is CA $77
CA $354 total
includes taxes & fees
Nov 18 - Nov 19
Beautiful home located in the Mad River Valley
A room with a large window overlooking a forest in autumn.

17. 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)
"It was perfect for my trip to central VT."
United States
Lyra F.
The price is CA $107
CA $391 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful home located in the Mad River Valley
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and trees.

18. Light-filled Bridges condo overlooking the mountains, by the free shuttle

Light-filled Bridges condo overlooking the mountains, by the free shuttle
Warren
8.8 out of 10, Excellent, (21 reviews)
"Great location and amenities. "
United States
Scott H.
The price is CA $108
CA $455 total
includes taxes & fees
Nov 14 - Nov 15
Light-filled Bridges condo overlooking the mountains, by the free shuttle
An outdoor seating area with Adirondack chairs, a stone fire pit, and a picnic table.

19. The Bridges condo with balcony, two saunas and free coffee and tea

The Bridges condo with balcony, two saunas and free coffee and tea
Warren
7.0 out of 10, Good, (4 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 CA $116
CA $316 total
includes taxes & fees
Nov 14 - Nov 15
The Bridges condo with balcony, two saunas and free coffee and tea
A wooden deck with a view of a forested mountain range.

20. The Bridges condo with forested views, three pools and two saunas

The Bridges condo with forested views, three pools and two saunas
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 CA $108
CA $499 total
includes taxes & fees
Nov 14 - Nov 15
The Bridges condo with forested views, three pools and two saunas
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

A row of Adirondack chairs in a lush green field with a backdrop of mist-covered hills and a purple sky.
Mad River Inn

Mad River Inn

Mad River Inn
Waitsfield

10/10 Excellent

This was a charming inn in the countryside of Vermont with beautiful mountains and valleys. Excellent location in the Mad River Valley to explore the small towns surrounding it!! Historic charm and very accommodating hosts. Friendly service. They are very Informative. Great breakfast as a bonus!! We would definitely recommend and would go back.
Canada
Oliva
Reviewed May 19, 2024
Mad River 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, 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 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlebury vacation rentals we have selected for you start as low as CA $106 per night. Entering your travel dates in the search wizard 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.

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.