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Vacation Homes in Middlebury

Modern farmhouse in classic VT orchard setting - stunning sunsets & location

2.0 star property
10.0 out of 10, Exceptional, (5)
"Great, spacious home in a classic Vermont setting. Beautiful views. Easy access to the cute towns of Vergennes, Middlebury, and Bristol."
Modern farmhouse in classic VT orchard setting - stunning sunsets & location

Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

8.6 out of 10, Excellent, (4)
"It was a great stay! Highly recommend "
Lakefront home near ski resorts with water view, dock, deck, fireplaces, & W/D

3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!

10.0 out of 10, Exceptional, (1)
"Very clean and easy to get to. "
The price is SAR 915
SAR 1,182 total
includes taxes & fees
10 Jun - 11 Jun
3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!

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

10.0 out of 10, Exceptional, (4)
"Great spot for 1-2 people and maybe a child. It was clean and affordable and had everything you need. "
The price is SAR 319
SAR 651 total
includes taxes & fees
10 Jun - 11 Jun
Cozy Tiny Home in charming Bristol VT, close to major ski areas

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (101)
"Perfect place to just get away for a few days and relax/unwind. Absolutely beautiful views and friendly neighborhood. Downtown was a convenient drive and Rutland is a short drive away for more choices to eat out. Truly enjoyed our stay!"
Water front home with large two tiered deck! 2 bathrooms 😂

Incredible Family Getaway Home With Boat Dock

10.0 out of 10, Exceptional, (135)
"Wonderful home with a great view. Would love to stay here again!"
Incredible Family Getaway Home With Boat Dock

NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

2.0 star property
10.0 out of 10, Exceptional, (1)
"Clean and nice, perfect mattresses on our beds, we enjoyed out stay."
NEW LISTING! Cozy Trotter (4-Bedroom Home) - Pets Allowed

Lakefront Killer Sunset Heaven

9.4 out of 10, Exceptional, (99)
"We had a super relaxing time at this property. The lake is virtually at the front porch. Beautiful setting. It was just what we needed. "
Lakefront Killer Sunset Heaven

Modern lakehouse w/ private beach, dock, fireplace, gym, theater, jacuzzi tub

Modern lakehouse w/ private beach, dock, fireplace, gym, theater, jacuzzi tub

Guest House surrounded by national forest

10.0 out of 10, Exceptional, (1)
"Beautiful house. Spectacular setting. Terrific hosts. "
Guest House surrounded by national forest

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (49)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

ADK Cozy River Cottage

10.0 out of 10, Exceptional, (40)
"Nice cabin"
ADK Cozy River Cottage

Ski home in the woods with a private hot tub & mountain views

9.8 out of 10, Exceptional, (43)
"Great time with 2 families with 4 kids. "
Ski home in the woods with a private hot tub & mountain views

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (71)
"Our second time staying here and once again it did not disappoint. Great location, spacious, and clean with all the amenities! Our family had a blast "
Middlebury Gem open concept and 5 minutes from town

The Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
The Bomoseen Bungalow: Vermont Lake House with Private Dock

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"My family of 8 stayed here for a ski vacation, and we loved it. Everything from the comfy beds, well equipped kitchen, space for ski equipment, and room for all of us to be together was perfect!! The hosts were Amazing! "
FiddleHead Lane-Near Killington, Fireplace, Grill

Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

10.0 out of 10, Exceptional, (182)
"Spectacular views were plentiful!"
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

WELCOME TO ON THE ROCK - A RECENTLY RENOVATED BEAUTIFUL LAKE FRONT HOME

10.0 out of 10, Exceptional, (9)
"Great location, with views of the north end of Lake George from the biggest deck on Lake George. Great boating, swimming and hiking."
WELCOME TO ON THE ROCK - A RECENTLY RENOVATED BEAUTIFUL LAKE FRONT HOME

1 Mi to Sugarbush Resort: Dog-Friendly Home!

9.4 out of 10, Exceptional, (3)
"Great place"
1 Mi to Sugarbush Resort: Dog-Friendly Home!

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (36)
"A perfect location for family weekend at Norwich University! We fit a family of 7 and all slept comfortably, lounged in the living room, or gathered in the spacious kitchen where I cooked and baked all weekend. We will definitely stay again!"
Classic Vermont Farmhouse near Sugarbush Resort
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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