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

Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Middlebury holiday 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 HK$3,089
HK$6,016 total
includes taxes & fees
7 Sept - 8 Sept
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, (1 review)
"Lovely home in a great location. Very comfortable and we had a great stay"
United States
carol m.
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.
The price is HK$906
HK$2,627 total
includes taxes & fees
30 Sept - 1 Oct
*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 HK$1,094
HK$2,869 total
includes taxes & fees
17 Sept - 18 Sept
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 HK$2,736
HK$2,982 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$2,532
HK$3,412 total
includes taxes & fees
1 Sept - 2 Sept
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 HK$3,837
HK$7,707 total
includes taxes & fees
1 Sept - 2 Sept
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 HK$743
HK$1,936 total
includes taxes & fees
3 Sept - 4 Sept
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
The price is HK$2,532
HK$3,395 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$2,362
HK$3,184 total
includes taxes & fees
13 Sept - 14 Sept
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 HK$1,043
HK$1,642 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$1,171
HK$2,716 total
includes taxes & fees
1 Sept - 2 Sept
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 HK$1,427
HK$2,950 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$2,193
HK$2,990 total
includes taxes & fees
9 Sept - 10 Sept
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.
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 HK$1,983
HK$4,539 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$2,193
HK$2,990 total
includes taxes & fees
9 Sept - 10 Sept
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 HK$2,110
HK$3,128 total
includes taxes & fees
31 Aug - 1 Sept
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.
The price is HK$2,362
HK$3,201 total
includes taxes & fees
17 Sept - 18 Sept
Inviting timber frame cabin in Vermont's Green Mountains
Desk, iron/ironing board, travel cot, 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 HK$2,348
HK$3,010 total
includes taxes & fees
1 Sept - 2 Sept
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
"The view was gorgeous and the rental home was perfect for few adults along with few kids. Would visit again! The lodge tap room was a delight each night and the boating rental and free boat access was enjoyed by all. We loved the access to sit in Adirondack chairs along the lake any time of day or night"
Raska 4-night trip
Posted 9 hours ago
Lake Bomoseen Lodge

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
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last

Look no further and take a look at our great range of rental properties in Middlebury!

Frequently asked questions

Are there holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Vermont Folklife Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Middlebury has to offer?

Breathtaking views from charming lakefront home on beautiful Lake George: This holiday home rental outside of Middlebury is located on a lake, and has a patio, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Middlebury?

Expedia has 16 holiday 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 holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.