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
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 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, (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.
The price is AED 1,543
AED 2,868 total
includes taxes & fees
1 Nov - 2 Nov
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
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 AED 581
AED 1,420 total
includes taxes & fees
27 Oct - 28 Oct
Purple Door Cottage in the heart of Middlebury!
A wooden cabin with a snow-covered roof, surrounded by trees and snow.

3. 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 AED 1,350
AED 1,472 total
includes taxes & fees
27 Oct - 28 Oct
Robert Frost Mountain Cabins
A modern kitchen with white cabinets, a coffee machine, and a wooden accent 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
Charming one bedroom just minutes to Middlebury!
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 AED 693
AED 1,446 total
includes taxes & fees
8 Nov - 9 Nov
Gracious two bedroom just minutes to Middlebury!
A spacious dining area with a long table set for six, large windows offering a view of the outdoors, and a wooden ceiling structure.

6. 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 AED 1,557
AED 3,304 total
includes taxes & fees
28 Oct - 29 Oct
Beautiful timber frame just minutes to Middlebury!
A kitchen with a large island, wooden ceiling beams, and various kitchen appliances.

7. 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 AED 544
AED 832 total
includes taxes & fees
8 Nov - 9 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

8. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is AED 625
AED 1,325 total
includes taxes & fees
8 Nov - 9 Nov
Tasteful two bedroom just minutes to Middlebury!
A cozy living room with a wooden ceiling, a fireplace, a television, and a comfortable seating area.

9. 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 AED 948
AED 1,294 total
includes taxes & fees
2 Nov - 3 Nov
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
A wooden cabin with a snow-covered roof, a porch with a green door, and a small window on the side.

10. 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 AED 948
AED 1,294 total
includes taxes & fees
2 Nov - 3 Nov
Inviting timber frame cabin in Vermont's Green Mountains
A wooden table with a bottle of wine, glasses, and grapes.

11. 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 AED 948
AED 1,294 total
includes taxes & fees
2 Nov - 3 Nov
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
A large, two-story cabin with a covered porch and a small deck, surrounded by dense forest.

12. 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 AED 948
AED 1,294 total
includes taxes & fees
2 Nov - 3 Nov
Cozy and pristine timberframe cabin
A covered porch with outdoor furniture, a ceiling fan, and a wooden deck.

13. Little City Big Heart

Little City Big Heart
Vergennes
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful home,very family friendly. The host is very welcoming and easy to get in contact with. Would recommend this property to family and friends."
United States
Craig S.
The price is AED 919
AED 1,701 total
includes taxes & fees
3 Nov - 4 Nov
Little City Big Heart
A snow-covered house with a lit entrance and a small outdoor light feature.

14. 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 AED 327
AED 839 total
includes taxes & fees
4 Nov - 5 Nov
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.

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

Beautiful Lake House with whole house renovation & fresh modern appeal!
Crown Point
9.6 out of 10, Exceptional, (14 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 AED 988
AED 1,466 total
includes taxes & fees
27 Oct - 28 Oct
Beautiful Lake House with whole house renovation & fresh modern appeal!
A lakeside house with a dock, surrounded by dense trees.

16. Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets

Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
Bridport
10.0 out of 10, Exceptional, (3 reviews)
"the home was very clean, plenty of space, there were many amenities which may the stay very pleasant."
United States
Robert H.
The price is AED 1,502
AED 3,154 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
A log cabin with a gravel driveway leading to it, surrounded by dense forest.

17. 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 AED 948
AED 1,294 total
includes taxes & fees
5 Nov - 6 Nov
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
A wooden staircase leading to a dock by a lake surrounded by trees.

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

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Leicester
8.0 out of 10, Very good, (2 reviews)
"Everything was spectacular! Fern Lake is peaceful and breathtaking. Lake house was wonderful, and amazing. It was spacious, yet homie."
United States
Eric A.
The price is AED 1,248
AED 2,637 total
includes taxes & fees
27 Oct - 28 Oct
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
An outdoor wood-burning stove with a view of the landscape in the background.

19. Serenity Now! - 20 mins from Middlebury College on Lake Champlain in Bridport VT

Serenity Now! - 20 mins from Middlebury College on Lake Champlain in Bridport VT
Bridport
The price is AED 1,469
AED 2,719 total
includes taxes & fees
31 Oct - 1 Nov
Serenity Now! - 20 mins from Middlebury College on Lake Champlain in Bridport VT
Exterior

20. 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 AED 948
AED 1,294 total
includes taxes & fees
8 Nov - 9 Nov
Immaculate mountain cabin with awe inspiring sunrise and mountain views
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

The Waitsfield Inn

The Waitsfield Inn

10/10 Excellent
"It’s a great inn. We really enjoyed our stay here and highly recommend it!"
Shourya 2-night trip
Posted 5 hours ago
The Waitsfield Inn

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.