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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middlebury vacation rentals

Coffee/tea maker, fridge, microwave, oven

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 AED 1,447
AED 2,793 total
includes taxes & fees
10 Sep - 11 Sep
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
Golf

2. 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.
The price is AED 833
AED 1,751 total
includes taxes & fees
3 Sep - 4 Sep
Purple Door Cottage in the heart of Middlebury!
Exterior

3. *Downtown Middlebury Waterfall Studio Apartment*

*Downtown Middlebury Waterfall Studio Apartment*
Middlebury
9.8 out of 10, Exceptional, (10 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*
Exterior detail

4. 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.
The price is AED 496
AED 1,322 total
includes taxes & fees
17 Sep - 18 Sep
Downtown Middlebury 3 BR Home - Walk Everywhere!
Exterior

5. 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 AED 1,231
AED 1,341 total
includes taxes & fees
3 Sep - 4 Sep
Robert Frost Mountain Cabins
Smart TV, fireplace, DVD player, books

6. 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 1,186
AED 1,599 total
includes taxes & fees
3 Sep - 4 Sep
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Interior

7. 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 1,882
AED 3,721 total
includes taxes & fees
22 Sep - 23 Sep
Beautiful timber frame just minutes to Middlebury!
Exterior detail

8. 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 AED 400
AED 974 total
includes taxes & fees
15 Sep - 16 Sep
Charming one bedroom just minutes to Middlebury!
Exterior

9. 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
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Interior

10. 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 AED 1,107
AED 1,500 total
includes taxes & fees
13 Sep - 14 Sep
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Coffee/tea maker, fridge, microwave, oven

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, (89 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 AED 384
AED 636 total
includes taxes & fees
3 Sep - 4 Sep
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Interior

12. Gracious two bedroom just minutes to Middlebury!

Gracious two bedroom just minutes to Middlebury!
New Haven
The price is AED 701
AED 1,467 total
includes taxes & fees
15 Sep - 16 Sep
Gracious two bedroom just minutes to Middlebury!
Interior

13. Tasteful two bedroom just minutes to Middlebury!

Tasteful two bedroom just minutes to Middlebury!
New Haven
The price is AED 569
AED 1,262 total
includes taxes & fees
3 Sep - 4 Sep
Tasteful two bedroom just minutes to Middlebury!
Exterior

14. 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 1,027
AED 1,401 total
includes taxes & fees
9 Sep - 10 Sep
Cozy and pristine timberframe cabin
Property grounds

15. 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.
The price is AED 1,248
AED 2,657 total
includes taxes & fees
3 Sep - 4 Sep
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Property grounds

16. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is AED 936
AED 2,134 total
includes taxes & fees
9 Sep - 10 Sep
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior

17. 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 AED 1,027
AED 1,393 total
includes taxes & fees
10 Sep - 11 Sep
Adorable cabin with screened porch and private fire pit
Smart TV, fireplace

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.
The price is AED 988
AED 1,466 total
includes taxes & fees
13 Sep - 14 Sep
Beautiful Lake House with whole house renovation & fresh modern appeal!
Exterior

19. 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.
Inviting timber frame cabin in Vermont's Green Mountains
Desk, iron/ironing board, travel crib, WiFi

20. 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.
The price is AED 1,100
AED 1,406 total
includes taxes & fees
6 Sep - 7 Sep
Little City Big Heart
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

Lake Bomoseen Lodge

Lake Bomoseen Lodge

10/10 Excellent
"Great location right near the lake. The pool was warm and clean. The rooms were spacious and accommodating. We had a great meal at the taproom. We will definitely be back."
Daniel 1-night trip
Posted 2 hours ago
Lake Bomoseen Lodge

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 16 vacation rentals for your stay in Middlebury.

What’s there to see and do in Middlebury?

Cultural attractions include Henry Sheldon Museum of Vermont History and Kevin P. Mahaney '84 Center for the Arts, whereas Green Mountain National Forest and Middlebury Falls 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.