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Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

Browse Select Middlebury Vacation Homes

Our top choices for Middlebury vacation homes

Cozy Tiny Home in charming Bristol VT, close to major ski areas
Outdoor dining

Cozy Tiny Home in charming Bristol VT, close to major ski areas

9.8 out of 10, Exceptional, (8)
"The camper was the perfect size, in the perfect location. Everything was truly perfect. The owners were welcoming and helpful. I would be delighted to stay again."
The price is CA $106
CA $227 total
includes taxes & fees
Aug 28 - Aug 29
Cozy Tiny Home in charming Bristol VT, close to major ski areas
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is CA $123
CA $231 total
includes taxes & fees
Sep 9 - Sep 10
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Make memories at this unique and family-friendly Vermont cabin!
Interior

Make memories at this unique and family-friendly Vermont cabin!

10.0 out of 10, Exceptional, (4)
"Loved the place! Just an hour from lake george! "
The price is CA $248
CA $406 total
includes taxes & fees
Sep 1 - Sep 2
Make memories at this unique and family-friendly Vermont cabin!
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Property grounds

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
The price is CA $138
CA $437 total
includes taxes & fees
Sep 1 - Sep 2
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Mad Mountain Meadows - Stunning Mountain Views!
Interior

Mad Mountain Meadows - Stunning Mountain Views!

10.0 out of 10, Exceptional, (1)
"Great house great location!"
The price is CA $237
CA $889 total
includes taxes & fees
Sep 3 - Sep 4
Mad Mountain Meadows - Stunning Mountain Views!
Beautiful Farmhouse Close to Warren Village and Sugarbush Resort
Outdoor dining

Beautiful Farmhouse Close to Warren Village and Sugarbush Resort

10.0 out of 10, Exceptional, (11)
"Very nice place. Thank you"
Beautiful Farmhouse Close to Warren Village and Sugarbush Resort
Cozy A-frame with loft, deck and easy ski access
Property grounds

Cozy A-frame with loft, deck and easy ski access

7.6 out of 10, Good, (7)
"The property had plenty of space for our group. I would suggest some steps be put in and some more care be spent on snow removal but we had fun sliding downhill to the entrance."
The price is CA $123
CA $642 total
includes taxes & fees
Sep 2 - Sep 3
Cozy A-frame with loft, deck and easy ski access
Beautiful home located in the Mad River Valley
Property grounds

Beautiful home located in the Mad River Valley

9.2 out of 10, Wonderful, (5)
"Good area"
Beautiful home located in the Mad River Valley
Ski, Hike & Relax. Warm 1BR Spot.
Terrace/patio

Ski, Hike & Relax. Warm 1BR Spot.

10.0 out of 10, Exceptional, (1)
"Mary clean and nice property owners were very pleasant and helpful. Would stay there again."
The price is CA $159
CA $209 total
includes taxes & fees
Sep 2 - Sep 3
Ski, Hike & Relax. Warm 1BR Spot.
Stunning Modern Retreat Overlooking The Mad River
Fridge, microwave, oven, stovetop

Stunning Modern Retreat Overlooking The Mad River

10.0 out of 10, Exceptional, (10)
"Great location! House was very nice and spacious. Definitely would book again! "
The price is CA $248
CA $974 total
includes taxes & fees
Sep 3 - Sep 4
Stunning Modern Retreat Overlooking The Mad River
The Brandon Inn - King Room
Exterior

The Brandon Inn - King Room

8.4 out of 10, Very good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is CA $256
CA $332 total
includes taxes & fees
Aug 28 - Aug 29
The Brandon Inn - King Room
Beautiful home located in the Mad River Valley
Property grounds

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (19)
"Great spot in the Mad River Valley. Great host and close to lots!"
Beautiful home located in the Mad River Valley
The Brandon Inn - Fourth Floor Queen Room
Exterior

The Brandon Inn - Fourth Floor Queen Room

8.8 out of 10, Excellent, (6)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is CA $201
CA $261 total
includes taxes & fees
Aug 28 - Aug 29
The Brandon Inn - Fourth Floor Queen Room
Large Vermont ski home on private scenic lot centrally located in the Mad River Valley
Terrace/patio

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

10.0 out of 10, Exceptional, (14)
"Wonderful ski house close to the mountain and a great house layout for young children / families!"
Large Vermont ski home on private scenic lot centrally located in the Mad River Valley
Gorgeous Mountain Home Near Mad River Glen
Interior

Gorgeous Mountain Home Near Mad River Glen

10.0 out of 10, Exceptional, (9)
"We enjoyed all the comforts with great proximity to the area. Love this house"
The price is CA $310
CA $1,078 total
includes taxes & fees
Sep 22 - Sep 23
Gorgeous Mountain Home Near Mad River Glen
The Brandon Inn - Double Room
Dining

The Brandon Inn - Double Room

8.0 out of 10, Very good, (1)
The price is CA $256
CA $333 total
includes taxes & fees
Sep 1 - Sep 2
The Brandon Inn - Double Room
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Fridge, microwave, oven, stovetop

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice place to stay. Very well equipped and clean."
The price is CA $404
CA $981 total
includes taxes & fees
Sep 14 - Sep 15
The Bomoseen Bungalow: Vermont Lake House with Private Dock
The Brandon Inn - Family Suite For Four
Dining

The Brandon Inn - Family Suite For Four

10.0 out of 10, Exceptional, (1)
"Very charming historic inn. Suite was perfect for our family of four. We all liked the historic elevator! The bar looked very nice and hopefully it will be open more consistently. The town had several good restaurants. We would stay here again for sure!"
The price is CA $297
CA $385 total
includes taxes & fees
Sep 1 - Sep 2
The Brandon Inn - Family Suite For Four
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
TV, fireplace, offices

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

10.0 out of 10, Exceptional, (13)
"We had a wonderful time and the place was great. We found everything we needed easily and loved the charm of the place. Perfect spot for a ski vacation just a few min from sugarbush and mad river."
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
Beautiful Country Home with Hot Tub & Pool Table
Interior

Beautiful Country Home with Hot Tub & Pool Table

10.0 out of 10, Exceptional, (1)
"It was really lovely. Very comfortable, easy to keep clean. Everyone loved the hot tub."
The price is CA $212
CA $1,042 total
includes taxes & fees
Aug 28 - Aug 29
Beautiful Country Home with Hot Tub & Pool Table
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

10/10 Excellent
"Excellent overall "
Mitchell 2-night trip
Posted 2 days ago
The Waitsfield Inn

Find out more about Middlebury

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
507
Accommodation
295 Vacation Homes
Lowest Price
CA $106
Highest Price
CA $409

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