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

Holiday Homes in Middlebury

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Check prices for these dates

In two weeks
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Middlebury holiday homes

Golf

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
The price is AU$613
includes taxes & fees
8 July - 9 July
Purple Door Cottage in the heart of Middlebury!
Fridge, microwave, oven, stovetop

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, (80 reviews)
"Lovely property. Will stay again."
United States
Patricia Y.
The price is AU$1,086
includes taxes & fees
15 July - 16 July
Updated Middlebury Home! Walk to Town, Sleeps Groups Comfortably
Interior

Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes

Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes
Bristol
9.8 out of 10, Exceptional, (23 reviews)
"Host and tiny house were fantastic!"
United States
Peter D.
The price is AU$247
includes taxes & fees
15 July - 16 July
Cozy Tiny Home in charming Bristol VT, close to skiing, hiking, swimming holes
Exterior detail

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
9.8 out of 10, Exceptional, (16 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
Fridge, microwave, oven, stovetop

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

Light-filled retreat in Mad River Valley with internet & deck
Fayston
10.0 out of 10, Exceptional, (5 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 AU$887
includes taxes & fees
4 July - 5 July
Light-filled retreat in Mad River Valley with internet & deck
Interior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (44 reviews)
"Very convenient to Warren center. This house served us well as we were able to bring our dog over the Christmas holiday. Perfect house for a family. "
United States
Monica R.
Beautiful home located in the Mad River Valley
Terrace/patio

Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.4 out of 10, Exceptional, (52 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
Property grounds

Studio in the country w/Hot Tub

Studio in the country w/Hot Tub
Monkton
The price is AU$372
includes taxes & fees
5 July - 6 July
Studio in the country w/Hot Tub
Interior

Traditional Vermont Ski Lodge minutes from Mad River Glen and Sugarbush

Traditional Vermont Ski Lodge minutes from Mad River Glen and Sugarbush
Fayston
10.0 out of 10, Exceptional, (1 review)
"We have a wonderful stay at this beautiful home near Waitsfield! It was comfortable and inviting and the kitchen had everything we needed to create a July 4th feast! The home was clean and spacious and very close to grocery stores and coffee shops and great restaurants. A 5 star vacation!"
United States
rachel k.
Traditional Vermont Ski Lodge minutes from Mad River Glen and Sugarbush
Interior

Luxurious Vermont home minutes from Sugarbush Resort

Luxurious Vermont home minutes from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (42 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
Terrace/patio

Large Vermont ski home on private scenic lot centrally located in the Mad River Valley

Large Vermont ski home on private scenic lot centrally located in the Mad River Valley
Waitsfield
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful ski house close to the mountain and a great house layout for young children / families!"
United States
Heather Bello T.
Large Vermont ski home on private scenic lot centrally located in the Mad River Valley
Fridge, microwave, oven, stovetop

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, (8 reviews)
"Perfect ski house!"
United States
Christina H.
The price is AU$1,058
includes taxes & fees
22 July - 23 July
Chalet Valhalla with Hot Tub right next to Sugarbush Resort
Smart TV, fireplace

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, (15 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
Smart TV

Moose Lodge - Rustic and Cozy

Moose Lodge - Rustic and Cozy
Ticonderoga
9.8 out of 10, Exceptional, (61 reviews)
"We had a great family get together. The lodge is beautiful and so much space. We loved it."
United States
Diane B.
The price is AU$1,124
includes taxes & fees
14 July - 15 July
Moose Lodge - Rustic and Cozy
Smart TV, fireplace, DVD player, video library

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
chittenden
10.0 out of 10, Exceptional, (31 reviews)
"We had a great time and enjoyed our stay."
United States
Nicole R.
The price is AU$1,298
includes taxes & fees
5 July - 6 July
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 10, Pet Friendly, Views & Grill
Terrace/patio

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, (1 review)
"This house has literally everything you would ever need. Even had a pack n play, kids towels, baby wipes, and a kids play mat. Would be nice to stay in warmer months to enjoy the lake."
United States
Nicholas A.
The price is AU$1,173
includes taxes & fees
12 July - 13 July
Waterfront 3BR/3BA — Summer Lake Escape, Fire Pit, Grill, Deck & Sunsets
Exterior detail

Modern Lake Champlain Lake House with Private Beach and Docks

Modern Lake Champlain Lake House with Private Beach and Docks
Charlotte
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home hosted by Scott! We had so much fun, the house is well stocked with everything (cooking, games, etc.). We can’t wait to come back."
United States
Michael W.
Modern Lake Champlain Lake House with Private Beach and Docks
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

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Clean, comfortable beds. Beautiful setting with great view outside our window."
John 2-night trip
Posted less than an hour ago
Courtyard Middlebury

Find out more about Middlebury

Middlebury Holiday Homes information

Number of reviews
8,070
Accommodation
283 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$371