Search Vacation Homes in Middlebury

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Middlebury holiday homes

Interior

Holiday Home in Bristol

Cozy Tiny Home in charming Bristol VT, close to major ski areas free ski voucher
9.8 out of 10, Exceptional, (18 reviews)
"This is a cozy place to stay. It is well cared for and in a pleasant location. We enjoyed our stay."
United States
Sue T.
The price is HK$633
HK$1,322 total
includes taxes & fees
9 Mar - 10 Mar
Cozy Tiny Home in charming Bristol VT, close to major ski areas free ski voucher
Marina

Holiday Home in Bomoseen

The Bomoseen Bungalow: Vermont Lake House with Private Dock
9.6 out of 10, Exceptional, (4 reviews)
"Nice place to stay. Very well equipped and clean."
United States
Rich S.
The Bomoseen Bungalow: Vermont Lake House with Private Dock
Interior

Holiday Home in East Warren

Top of the Hill Modern Retreat
9.8 out of 10, Exceptional, (7 reviews)
"Really nice place everything was top notch. "
United States
Michael Q.
The price is HK$1,385
HK$5,345 total
includes taxes & fees
8 Mar - 9 Mar
Top of the Hill Modern Retreat
Interior

Holiday Home in Warren

Beautiful home located in the Mad River Valley
9.6 out of 10, Exceptional, (40 reviews)
"The place was spacious, but small, which I loved! Plenty of hot water, great communication with owner, plenty of extra chairs and the leaf for the table was fantastic!"
United States
Michael M.
Beautiful home located in the Mad River Valley
Smart TV, fireplace

Holiday Home in Crown Point

Beautiful Lake House with whole house renovation & fresh modern appeal!
10.0 out of 10, Exceptional, (11 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 HK$2,985
HK$4,255 total
includes taxes & fees
6 Mar - 7 Mar
Beautiful Lake House with whole house renovation & fresh modern appeal!
Property grounds

Holiday Home in Monkton

Studio in the country w/Hot Tub
The price is HK$1,054
HK$1,897 total
includes taxes & fees
9 Mar - 10 Mar
Studio in the country w/Hot Tub
Exterior

Holiday Home in Waitsfield

Cozy A-frame with loft, deck and easy ski access
7.4 out of 10, Good, (8 reviews)
"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."
United States
Jason F.
The price is HK$921
HK$3,912 total
includes taxes & fees
16 Mar - 17 Mar
Cozy A-frame with loft, deck and easy ski access
Living area

Holiday Home in Crown Point

Fisherman’s Cove on Lake Champlain – A Private Waterfront Getaway
The price is HK$1,249
HK$2,822 total
includes taxes & fees
9 Mar - 10 Mar
Fisherman’s Cove on Lake Champlain – A Private Waterfront Getaway
Exterior

Holiday Home in Warren

Beautiful home located in the Mad River Valley
9.2 out of 10, Wonderful, (9 reviews)
"Host was awesome and very responsive to our needs. We couldn't have had sla nicer stay. "
United States
Marlene P.
Beautiful home located in the Mad River Valley
Exterior

Holiday Home in Warren

Beautiful home located in the Mad River Valley
10.0 out of 10, Exceptional, (23 reviews)
"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."
United States
kevin m.
Beautiful home located in the Mad River Valley
Interior

Holiday Home in Crown Point

Charming 3-bedroom house in Crown Point with WiFi and AC
9.8 out of 10, Exceptional, (7 reviews)
"We had a very good stay at this property. Very clean and beautiful view of the lake. Overall a relaxing stay with family "
United States
Kaitlynd K.
The price is HK$2,732
HK$4,939 total
includes taxes & fees
31 Mar - 1 Apr
Charming 3-bedroom house in Crown Point with WiFi and AC
Fridge, microwave, oven, stovetop

Holiday Home in Fayston

Chalet Valhalla with Hot Tub right next to Sugarbush Resort
10.0 out of 10, Exceptional, (6 reviews)
"The hot tub was very nice and the stay was LOVELY. "
United States
Nicole B.
The price is HK$1,451
HK$5,933 total
includes taxes & fees
24 Mar - 25 Mar
Chalet Valhalla with Hot Tub right next to Sugarbush Resort
Property grounds

Holiday Home in Bristol

Private 5-Acre Escape | Pool, Lake & Gardens
The price is HK$1,231
HK$4,413 total
includes taxes & fees
8 Mar - 9 Mar
Private 5-Acre Escape | Pool, Lake & Gardens
Smart TV, offices

Holiday Home in Waitsfield

Beautiful Family Home Central to Mad River Valley
10.0 out of 10, Exceptional, (12 reviews)
"Fantastic house and property in a beautiful area. We had a great stay and everything was wonderful."
United States
Greg L.
The price is HK$2,831
HK$7,872 total
includes taxes & fees
19 Mar - 20 Mar
Beautiful Family Home Central to Mad River Valley
Exterior detail

Holiday Home in East Warren

Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
9.8 out of 10, Exceptional, (15 reviews)
"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."
United States
John B.
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
Terrace/patio

Holiday Home in Warren

Classic Vermont Farmhouse near Sugarbush Resort
9.6 out of 10, Exceptional, (49 reviews)
"Charming older home, clearly well loved. Enjoyed eating on the back porch, the generous living room space, and the sinks in every bedroom!"
United States
Nathalie B.
Classic Vermont Farmhouse near Sugarbush Resort
Property grounds

Holiday Home in Leicester

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock
Exterior

Holiday Home in Bridport

Waterfront 3 Bedroom 3 Bathroom Large House in Bridport—Fire pit, Grill, Deck
The price is HK$2,124
HK$4,696 total
includes taxes & fees
6 Mar - 7 Mar
Waterfront 3 Bedroom 3 Bathroom Large House in Bridport—Fire pit, Grill, Deck
Outdoor spa tub

Holiday Home in Waitsfield

Breathtaking Views 7 Bedroom Estate w/Hot Tub
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home with a spacious and open kitchen! The views from every window we like a portrait. "
United States
Belinda
The price is HK$3,883
HK$10,697 total
includes taxes & fees
5 Apr - 6 Apr
Breathtaking Views 7 Bedroom Estate w/Hot Tub
Smart TV, offices, computer monitors

Holiday Home in East Warren

Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views
10.0 out of 10, Exceptional, (10 reviews)
"Great place for our gathering of 9."
United States
JoAnn L.
Sugarbush Vista - 4000sq. ft. Estate with Hot Tub & Mountain Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebury Hotel Reviews

Middlebury Inn

Middlebury Inn

10/10 Excellent
"Lovely hotel in a stunning location. The ambience is stellar. The rooms are spacious and cozy. Bedding, bathrooms, beds, view from the room, etc. were all top notch. I would have loved to stay here for more than one night. I'll be back sometime to visit again. "
Kimm 1-night trip
Posted 5 days ago
Middlebury Inn

Find out more about Middlebury

Middlebury Vacation Homes information

Number of reviews
206
Accommodation
282 Vacation Homes
Lowest Price
HK$1,322
Highest Price
HK$10,697

Explore a world of travel with Expedia