Middlebury, VT Vacation Homes from ￥29,025

A wooden pier extending into a lake, surrounded by lush greenery and a prominent lighthouse on a small island.

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Our top choices for Middlebury vacation homes

A large grassy field with a historic building in the background.

1. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

￥64,752 total

includes taxes & fees

Oct 19 - Oct 20

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

2. Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

Middlebury

Page E.

￥121,244 total

includes taxes & fees

Nov 1 - Nov 2

A wooden interior with large windows, a dining table, chairs, and a sofa.

3. Beautiful timber frame just minutes to Middlebury!

New Haven

"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...

Suzanne L.

￥140,052 total

includes taxes & fees

Oct 21 - Oct 22

A rustic cabin surrounded by autumn foliage.

4. Beautiful home located in the Mad River Valley

Warren

Allie T.

5. Beautiful home located in the Mad River Valley

Warren

Sloan S.

A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

6. Studio in the country w/Hot Tub

Monkton

￥40,973 total

includes taxes & fees

Oct 19 - Oct 20

A modern living room with a fireplace, a sofa, a coffee table, and a white door.

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

Crown Point

Phillip K.

￥63,050 total

includes taxes & fees

Oct 19 - Oct 20

A two-story house with a covered porch, outdoor seating, and a lawn.

8. Classic Vermont Farmhouse near Sugarbush Resort

Warren

Peggy V.

A wooden cabin interior with a staircase leading to a balcony, large windows, and a view of a snowy forest.

9. Large multi-family ski home located on the slopes of Sugarbush Resort

Warren

James K.

A wooden staircase leading to a dock by a lake surrounded by trees.

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

Leicester

Eric A.

￥114,331 total

includes taxes & fees

Oct 19 - Oct 20

A lakeside setting with a fire pit and a bench near the water.

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

Bridport

Robert H.

￥135,710 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living area with a green leather sofa, a wooden dining table, and a kitchen in the background.

12. The Longhorn - Inspired 5br 3ba Home with Hot Tub

Fayston

Steve P.

￥139,645 total

includes taxes & fees

Oct 22 - Oct 23

A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

13. Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

East Warren

Daniel B.

A modern living room with a sofa, coffee table, and a flat-screen TV mounted on the wall.

14. The Hinesburg Hideaway Unit 3

Hinesburg

William

￥29,025 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck with a metal railing, black plastic chairs, and a large window overlooking a forested area.

15. Glamping Escape House - reconnect with nature without giving up comfort.

Ticonderoga

"Enjoyed a three night stay with family. The listing is very accurate. This is glamping. If that is what you are expecting you should be delighted. Some nice additional highlights were an ample source of firewood, nice swings, a battery operated fan. Also, the shower was a pleasant surprise. I was not expecting a hot shower. It is a great system. I would say it provides about a one yard reservoir providing heated water. Very nice. Hosts were very helpful and went above and beyond to...

patricia A.

￥31,605 total

includes taxes & fees

Oct 19 - Oct 20

A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

16. Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace

Hancock

Katie H.

￥177,707 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living area with a fireplace, a curved staircase, and large windows offering views of the outdoors.

17. The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views

East Warren

Brian S.

￥218,573 total

includes taxes & fees

Oct 22 - Oct 23

An outdoor seating area with wicker chairs and a small table, surrounded by lush greenery and trees.

18. Entire Enchanting, Light-Filled 1830 Farmhouse

Waitsfield

Patti M.

￥113,863 total

includes taxes & fees

Oct 19 - Oct 20

A wooden deck with a hot tub and seating, overlooking a scenic landscape.

19. Sky Zen - Ridge Line Retreat

East Warren

Spyridon M.

￥161,885 total

includes taxes & fees

Nov 8 - Nov 9

A house with a stone staircase leading to a wooden deck, surrounded by trees and autumn leaves.

20. Modern Lake Champlain Lake House with Private Beach and Docks

Charlotte

Jennifer G.

￥170,434 total

includes taxes & fees

Oct 25 - Oct 26

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Top Middlebury Hotel Reviews

Mad River Lodge

8/10 Good

"Staff was very helpful and friendly. Room was a little small but worked out well."

The Mountain Top Inn & Resort

10/10 Excellent

"Wow! We are still wondering how we lucked out finding this place. The staff was so nice and helpful. The room was warm and welcoming. The food in the dining room was delicious. We enjoyed the comforting coffee in the lobby. But we will be talking about the view of the lake and lovely peak fall foliage for years to come! This was a great place for us to call base for a few days and would love to come back again!"

Brandon Inn

10/10 Excellent

"The Brandon Inn was lovely- clean, comfortable and the staff were all amazingly helpful, cheerful and fun. To note, I have severe fragrance allergies but there were no scents or perfumes added to the linens or the rooms- I was so grateful! The only "issue" was the severe lack of water pressure and tepid temperature "hot' water in my 3rd floor suite. It was disappointing. They referred me to 22Park Eatery (next door) for dinner since their dining room was closed due to a private wedding (I didn't know that in advance) - and it was an excellent referral! So grateful. I'd stay here again without hesitation."

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews	236
Accommodation	297 Vacation Homes
Lowest Price	￥29,025
Highest Price	￥218,573

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlebury vacation homes

1. Purple Door Cottage in the heart of Middlebury!

2. Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably

3. Beautiful timber frame just minutes to Middlebury!

4. Beautiful home located in the Mad River Valley