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

Middlebury Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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!

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 CA $281
CA $611 total
includes taxes & fees
Oct 27 - Oct 28
Purple Door Cottage in the heart of Middlebury!
A wooden interior with large windows, a dining table, chairs, and a sofa.

2. 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 CA $540
CA $1,180 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful timber frame just minutes to Middlebury!
A rustic cabin surrounded by autumn foliage.

3. 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 bedroom with a bed, bedside table, lamp, and a ceiling fan.

4. 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 CA $339
CA $632 total
includes taxes & fees
Oct 6 - Oct 7
Little City Big Heart
A modern kitchen with wooden cabinets, stainless steel appliances, and large windows offering a view of the outdoors.

5. Chalet Valhalla with Hot Tub right next to Sugarbush Resort

Chalet Valhalla with Hot Tub right next to Sugarbush Resort
Fayston
10.0 out of 10, Exceptional, (10 reviews)
"The hot tub was very nice and the stay was LOVELY. "
United States
Nicole B.
The price is CA $114
CA $889 total
includes taxes & fees
Sep 29 - Sep 30
Chalet Valhalla with Hot Tub right next to Sugarbush Resort
A modern living room with a sofa, coffee table, and a flat-screen TV mounted on the wall.

6. The Hinesburg Hideaway Unit 3

The Hinesburg Hideaway Unit 3
Hinesburg
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and spacious, quick communication with host."
United States
Tina C.
The price is CA $204
CA $260 total
includes taxes & fees
Oct 5 - Oct 6
The Hinesburg Hideaway Unit 3
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!

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 CA $381
CA $555 total
includes taxes & fees
Sep 29 - Sep 30
Beautiful Lake House with whole house renovation & fresh modern appeal!
A rustic cabin surrounded by autumn foliage.

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

10. Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is CA $210
CA $365 total
includes taxes & fees
Oct 6 - Oct 7
Studio in the country w/Hot Tub
A room with a large window overlooking a forest in autumn.

11. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (49 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 wooden staircase leading to a dock by a lake surrounded by trees.

12. 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 CA $481
CA $1,018 total
includes taxes & fees
Sep 29 - Sep 30
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
A wooden cabin interior with a staircase leading to a balcony, large windows, and a view of a snowy forest.

13. 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.

14. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.6 out of 10, Exceptional, (57 reviews)
Classic Vermont Farmhouse near Sugarbush Resort
A yellow building with a green roof and large windows overlooking a snowy landscape with trees and mountains.

15. Vermont Post & Beam w/Hot Tub & Stunning Views

Vermont Post & Beam w/Hot Tub & Stunning Views
Waitsfield
9.8 out of 10, Exceptional, (26 reviews)
"Beautiful spot, clean house and everything we needed for a relaxing time. Will be returning"
United States
William W.
The price is CA $215
CA $1,261 total
includes taxes & fees
Sep 30 - Oct 1
Vermont Post & Beam w/Hot Tub & Stunning Views
A wooden deck with a metal railing, black plastic chairs, and a large window overlooking a forested area.

16. 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)
The price is CA $219
CA $280 total
includes taxes & fees
Sep 30 - Oct 1
Glamping Escape House - reconnect with nature without giving up comfort.
A log cabin interior with a stone fireplace, a sofa set, a round table, and a large window offering a view of the outdoors.

17. Ridge House - Modern Log Home Nestled on top of a Private Mountain

Ridge House - Modern Log Home Nestled on top of a Private Mountain
Waitsfield
10.0 out of 10, Exceptional, (17 reviews)
"A gorgeous house, well designed, incredibly comfortable & perfectly appointed. Responsive staff at the mgmt company too. We will be back!"
United States
lauren m.
Ridge House - Modern Log Home Nestled on top of a Private Mountain
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.
The price is CA $365
CA $1,516 total
includes taxes & fees
Oct 1 - Oct 2
Breathtaking Views 7 Bedroom Estate w/Hot Tub
A kitchen with wooden beams, a central island, and a view of a snowy outdoor area.

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

Light-filled retreat in Mad River Valley with internet & deck
Fayston
8.8 out of 10, Excellent, (6 reviews)
"Enjoyed the comfortable home. Had just about everything we needed for our stay. Loved the location and the view was great. Close to things we wanted to do and see."
United States
Anonymous traveller
The price is CA $238
CA $862 total
includes taxes & fees
Oct 19 - Oct 20
Light-filled retreat in Mad River Valley with internet & deck
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

20. 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 CA $711
CA $1,345 total
includes taxes & fees
Oct 2 - Oct 3
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
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

White Horse Lodge

White Horse Lodge

10/10 Excellent
"Dana was very helpful."
Noralee 2-night trip
Posted 1 hour ago
White Horse Lodge

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
331
Accommodation
301 Vacation Homes
Lowest Price
CA $260
Highest Price
CA $1,824

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