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Compare 291 Vacation Homes in Middlebury with updated reviews, rates, and availability.

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

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 AED 841
AED 1,087 total
includes taxes & fees
4 Jun - 5 Jun
3-bedroom townhome in tranquil Ticonderoga with AC, WiFi close to Lake George!

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 😂

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 AED 312
AED 638 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Tiny Home in charming Bristol VT, close to major ski areas

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

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

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

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

Charming 3-bedroom house in Crown Point with WiFi and AC

10.0 out of 10, Exceptional, (2)
"Beautiful home and setting. Quiet and relaxing. Close to various points of interest. Thank you for sharing your home. We loved our stay."
Charming 3-bedroom house in Crown Point with WiFi and AC

Cute, Renovated Historic Home on River, Walk to Downtown

9.6 out of 10, Exceptional, (9)
"I really enjoyed my month here in Brandon and 19 River. I would stay here again!"
Cute, Renovated Historic Home on River, Walk to Downtown

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

Downtown Middlebury River House

Downtown Middlebury River House

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

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

Moose Lodge - Rustic and Cozy

9.8 out of 10, Exceptional, (50)
"Everything was great., the hike nearby is a plus! "
Moose Lodge - Rustic and Cozy

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

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
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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