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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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!

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 £366
includes taxes & fees
15 Oct - 16 Oct
Purple Door Cottage in the heart of Middlebury!
A modern kitchen with a central island, stainless steel appliances, and a large window.

2. 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, (83 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 £585
includes taxes & fees
1 Nov - 2 Nov
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
A room with a large window overlooking a forest in autumn.

3. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (50 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

4. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

5. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.0 out of 10, Wonderful, (12 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
Beautiful home located in the Mad River Valley
A wooden interior with large windows, a dining table, chairs, and a sofa.

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 £768
includes taxes & fees
13 Oct - 14 Oct
Beautiful timber frame just minutes to Middlebury!
A rural property with a wooden shed, a small cabin, and a well-maintained lawn.

7. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is £200
includes taxes & fees
13 Oct - 14 Oct
Studio in the country w/Hot Tub
A modern living room with a fireplace, a sofa, a coffee table, and a white door.

8. 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 £301
includes taxes & fees
13 Oct - 14 Oct
Beautiful Lake House with whole house renovation & fresh modern appeal!
A room with a large window overlooking a deck with two chairs and a table.

9. Luxurious Vermont home minutes from Sugarbush Resort

Luxurious Vermont home minutes from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (44 reviews)
"Perfect location for ski vacation. House was clean, close to resort. Quick drive to restaurants, looking forward to staying again! "
United States
Noah S.
Luxurious Vermont home minutes from Sugarbush Resort
A wooden cabin interior with a staircase leading to a balcony, large windows, and a view of a snowy forest.

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

Large multi-family ski home located on the slopes of Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (31 reviews)
"The skiing was fantastic. Thanks for a great stay."
United States
James K.
Large multi-family ski home located on the slopes of Sugarbush Resort
A two-story house with a covered porch, outdoor seating, and a lawn.

11. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.4 out of 10, Exceptional, (59 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
Classic Vermont Farmhouse near Sugarbush Resort
A lakeside setting with a fire pit and a bench near the water.

12. 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 £642
includes taxes & fees
13 Oct - 14 Oct
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
A modern living room with a sofa, coffee table, and a flat-screen TV mounted on the wall.

13. The Hinesburg Hideaway Unit 3

The Hinesburg Hideaway Unit 3
Hinesburg
9.4 out of 10, Exceptional, (6 reviews)
"Very clean, comfortable, and quiet. Newly renovated. Like a little townhouse apartment."
United States
William
The price is £142
includes taxes & fees
20 Oct - 21 Oct
The Hinesburg Hideaway Unit 3
A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

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

Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
East Warren
9.6 out of 10, Exceptional, (18 reviews)
"Great location, plenty of space, everything in house worked as described. Thank you!!"
United States
Daniel B.
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
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.

Glamping Escape House - reconnect with nature without giving up comfort.
Ticonderoga
9.4 out of 10, Exceptional, (3 reviews)
"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...
United States
patricia A.
The price is £154
includes taxes & fees
13 Oct - 14 Oct
Glamping Escape House - reconnect with nature without giving up comfort.
A modern living room with a large window overlooking a forested mountain landscape.

16. Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views

Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views
East Warren
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful comfortable place with the best view in the valley. All the amenities you need for great vacation. "
United States
Jeff C.
Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views
An outdoor seating area with wicker chairs and a small table, surrounded by lush greenery and trees.

17. Entire Enchanting, Light-Filled 1830 Farmhouse

Entire Enchanting, Light-Filled 1830 Farmhouse
Waitsfield
9.8 out of 10, Exceptional, (10 reviews)
"We came up to Vermont for a wedding and the "farm house" was just what we needed. Thank you! Much appreciated the easy check in and allowing us to arrive a bit earlier to get ready for the wedding bash. P. Murray"
United States
Patti M.
The price is £553
includes taxes & fees
19 Oct - 20 Oct
Entire Enchanting, Light-Filled 1830 Farmhouse
A hot tub on a wooden deck with a mountain view.

18. Breathtaking Views 7 Bedroom Estate w/Hot Tub

Breathtaking Views 7 Bedroom Estate w/Hot Tub
Waitsfield
10.0 out of 10, Exceptional, (16 reviews)
"Place was great"
United States
Christopher W.
Breathtaking Views 7 Bedroom Estate w/Hot Tub
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

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

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Hancock
10.0 out of 10, Exceptional, (1 review)
"The maple castle was awesome! Definitely the most unique house I have ever stayed in. You can sit in the hot tub and watch the river or you can walk down a tiny hill to tie up a tube and float in it. The owners were extremely helpful and responsive. Would definitely recommend. "
United States
Katie H.
The price is £1,051
includes taxes & fees
25 Oct - 26 Oct
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
A wooden deck with a hot tub and seating, overlooking a scenic landscape.

20. Sky Zen - Ridge Line Retreat

Sky Zen - Ridge Line Retreat
East Warren
10.0 out of 10, Exceptional, (1 review)
"We've stayed multiple times in this property and it's always been great. Beautiful house, landscape, and of course the views. The house is always very clean and well maintained. We look forward to our next stay here."
United States
Spyridon M.
Sky Zen - Ridge Line Retreat
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

8/10 Good
"Clean room .very few amenities. Continental breakfast is what it is. Cereal,toast, yogurt. Good place to stay for a night or 2"
Dennis 2-night trip
Posted 9 hours ago
The Waitsfield Inn

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews
332
Accommodation
297 Holiday Homes
Lowest Price
£142
Highest Price
£1,051