Middlebury Vacation Rentals
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Vacation Rentals in Middlebury
Beautiful 4-Bedroom Home beside Middlebury College
Middlebury VT
With a stay at this vacation home in Middlebury, you'll be within a 5-minute walk of Middlebury College and Emma Willard House.
Kitchen
Washer
The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views
Warren VT
With a stay at this vacation home in Warren (East Warren), you'll be within a 15-minute drive of Sugarbush Ski Resort and Mad River Valley.
Hot Tub
Kitchen
Killington Vermont Ski and Snowmobiling House
Pittsfield VT
With a stay at this vacation home in Pittsfield, you'll be within a 15-minute drive of Killington Resort and Green Mountain National Forest.
Hot Tub
Kitchen
3-bedroom house in fabulous Crown Point, New York. On Lake Champlain
Crown Point NY
With a stay at this vacation home in Crown Point, you'll be within a 5-minute drive of War Cannon Spirits and Gunnison Lakeshore Orchards.
Kitchen
Washer
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
Addison VT
When you stay at this vacation home in Vergennes, you'll be on the beach, within a 5-minute drive of D. A. R. State Park and Champlain Bridge Marina.
Hot Tub
Kitchen
Cozy Tiny Home in charming Bristol VT, close to major ski areas
Bristol VT
$147 nightly
The price is $164 total per night
$164 total
Dec 8 - Dec 9
Total with taxes and fees
With a stay at this vacation home in Bristol, you'll be a 3-minute walk from Winona Recreation Area and within a 5-minute drive of Lawrence Memorial Library.
Kitchen
Air conditioning
Classic Vermont Farmhouse near Sugarbush Resort
Warren VT
With a stay at this vacation home in Warren, you'll be in the mountains, within a 10-minute drive of Sugarbush Ski Resort and Green Mountain National Forest.
Kitchen
Washer
Vermont Post & Beam w/Hot Tub & Stunning Views
Waitsfield VT
With a stay at this vacation home in Waitsfield, you'll be within a 15-minute drive of Sugarbush Ski Resort and Mad River Valley.
Hot Tub
Kitchen
Private 5BR mt. view, pool, new hot tub, & fireplace!
Waitsfield VT
With a stay at this vacation home in Waitsfield, you'll be in the mountains, just steps from Mad River Valley and a 5-minute drive from Skinner Barn.
Pool
Hot Tub
Gorgeous Mountain Home Near Mad River Glen
Fayston VT
$1,344 nightly
The price is $1,505 total per night
$1,505 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
With a stay at this vacation home in Waitsfield, you'll be in the mountains, within a 15-minute drive of Sugarbush Ski Resort and Mad River Valley.
Kitchen
Washer
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.
Middlebury Vacation Rentals essential information
Accommodation | 282 Vacation Rentals |
|---|---|
Lowest Price | $164 |
Highest Price | $1,505 |
Popular accommodation | Beautiful 4-Bedroom Home beside Middlebury College, The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views, Killington Vermont Ski and Snowmobiling House, 3-bedroom house in fabulous Crown Point, New York. On Lake Champlain, Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!, Cozy Tiny Home in charming Bristol VT, close to major ski areas, Classic Vermont Farmhouse near Sugarbush Resort, Vermont Post & Beam w/Hot Tub & Stunning Views, Private 5BR mt. view, pool, new hot tub, & fireplace!, Gorgeous Mountain Home Near Mad River Glen, Historic home on 1 acre with snowmobile trails in backyard & mountain views, Water front home with large two tiered deck! 2 bathrooms 😂 |