Middlebury Holiday Homes from €168: Search Top House Rentals

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 holiday homes

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

1. Purple Door Cottage in the heart of Middlebury!

Middlebury

carol m.

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

1 Nov - 2 Nov

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.

includes taxes & fees

26 Oct - 27 Oct

A room with a large window overlooking a forest in autumn.

4. Beautiful home located in the Mad River Valley

Warren

Melissa P.

A rustic cabin surrounded by autumn foliage.

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

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

22 Oct - 23 Oct

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.

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

12. 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.

13. The Hinesburg Hideaway Unit 3

Hinesburg

Francis

includes taxes & fees

27 Oct - 28 Oct

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

14. 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.

includes taxes & fees

25 Oct - 26 Oct

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

15. Entire Enchanting, Light-Filled 1830 Farmhouse

Waitsfield

Patti M.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

25 Oct - 26 Oct

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

17. Sky Zen - Ridge Line Retreat

East Warren

Spyridon M.

includes taxes & fees

8 Nov - 9 Nov

A kitchen with wooden beams, a central island, and a view of a snowy outdoor area.

18. Light-filled retreat in Mad River Valley with internet & deck

Fayston

Anonymous traveller

includes taxes & fees

22 Oct - 23 Oct

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

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

Charlotte

Jennifer G.

includes taxes & fees

1 Nov - 2 Nov

20. Wilder Farm--Charming Vermont Farmhouse in Mad River Valley

Waitsfield

includes taxes & fees

22 Oct - 23 Oct

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Top Middlebury Hotel Reviews

Emrose Luxury Cabins

10/10 Excellent

"Such great atmosphere, thank you so much for making my birthday so wonderful"

Swift House Inn

10/10 Excellent

"LOVED our stay. Just sorry it was only for one night. The property is delightful and well maintained. Perfectly located for visiting Middlebury College. We took our dog and the welcome basket for her was adorable! We had dinner at Jessica's which was fantastic; great food and service and a thoroughly good experience all round. Breakfast in the morning was similarly excellent. Would definitely recommend the Swift Inn, and I hope we will have the opportunity to return."

Cozy Loft for two with Hot Tub & Mtn Views

10/10 Excellent

"Just perfect! Amazing, romantic, little cabin in the woods. Loved the hot tub, fire pit and hammock Attention to detail of owner was definitely noted. Communication was excellent. Would love to come back and spend more time at this awesome place!!"

Mad River Lodge

8/10 Good

"Unique building in an outdoor area. 3 stories with elevator between 1&2. Third (for 3 rooms) only reached via stairs. Nice common area with coffee, tea, microwave and snacks for purchase. Our room under the eves was comfortable once we were told about heating thermostat. Innkeeper very friendly and accommodating."

Basin Harbor

10/10 Excellent

"I had a nice time at the resort my room was nice and clean stuff was helpful and accommodating food was delicious property has two restaurants in a short distance it’s out of the way of big cities so it’s nice and quiet I went there with a specific intend of photographing fall foliage and I got some pretty shots of sunset over the lake Champlain. I will definitely return to this resort again"

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews	254
Accommodation	291 Holiday Homes
Lowest Price	€168
Highest Price	€1,231

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlebury holiday 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