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Compare 228 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Pristene lakefront property - charming, quiet, and rustic for nature lovers.

8.0 out of 10, Very Good, (71)
"Plenty of room for the whole family."
Pristene lakefront property - charming, quiet, and rustic for nature lovers.

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

10.0 out of 10, Exceptional, (176)
"Loved our stay! This home is so comfortable, clean, and the most breathtaking views of the lake. Enjoyed ice fishing at the bridge nearby and Vergennes has great shops and restaurants. Highly recommend! Thanks for a wonderful stay!"
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (23)
"Had a wonderful stay! Was cozy, clean, with a well stocked kitchen. Highly recommend. Evan was a lovely host. "
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

NEW! Modern Log Cabin with Skiing & Work-Friendly Setup

10.0 out of 10, Exceptional, (1)
"We went skiing with another family at Sugarbush. Location was great. House was cozy and comfortable"
NEW! Modern Log Cabin with Skiing & Work-Friendly Setup

Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

9.2 out of 10, Wonderful, (115)
"Lovely home with beautiful views. Very quiet and very comfortable on a cold windy weekend. Would be even more lovely in the summer!"
Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak

Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak

Top of the Hill Modern Retreat

10.0 out of 10, Exceptional, (1)
"I love this place! New and spacious. The kitchen has everything you need for the stay. My wife loves cooking in there. The only complaint is the water pressure is too weak. It is definite worth for families who love to cook."
The price is AED 802
AED 2,453 total
includes taxes & fees
26 Mar - 27 Mar
Top of the Hill Modern Retreat

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is AED 533
AED 689 total
includes taxes & fees
24 Feb - 25 Feb
The Brandon Inn - Fourth Floor Queen Room

Beautiful lake house on Lake Champlain!

9.8 out of 10, Exceptional, (95)
"Beautiful lake views on this lakefront property. Clean, well appointed and great communication with property manager. Would definitely return- thank you for a lovely visit!"
Beautiful lake house on Lake Champlain!

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (70)
"House is a perfect option for families visiting Middlebury College. Spacious, clean, and well appointed!"
Middlebury Gem open concept and 5 minutes from town

Historic home on 1 acre with snowmobile trails in backyard & mountain views

9.8 out of 10, Exceptional, (19)
"Very handy to ski either Sugarbush or MRG. All the comforts of home. Rustic and very clean property. "
Historic home on 1 acre with snowmobile trails in backyard & mountain views

Dog-friendly, three-story home with fireplace and washer/dryer - near Sugarbush

9.8 out of 10, Exceptional, (8)
"This is an exceptional rental. We have stayed at many locations in and around Sugarbush over the years and somehow missed this one--our new favorite. Beautiful house, great location, nice all-around vibe. Will definitely rent again."
Dog-friendly, three-story home with fireplace and washer/dryer - near Sugarbush

Moose Lodge - Rustic and Cozy

9.8 out of 10, Exceptional, (49)
"Everything was great., the hike nearby is a plus! "
Moose Lodge - Rustic and Cozy

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

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House

Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace

9.6 out of 10, Exceptional, (24)
"The home was immaculate and very comfortable. Many options for gathering together in or outdoors as well as peaceful spaces for drawing or reading. Well equiped and highly recommended!"
Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace

Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym~

10.0 out of 10, Exceptional, (4)
"Such a great house! Perfect location, wonderful amenities and fabulous host! Couldn’t have asked for a better home for our October weekend! Will definitely be back!"
Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym~

4 Mi to Sugarbush Resort: Waitsfield Retreat

9.2 out of 10, Wonderful, (47)
"The location of the house was good for Bolton Valley, and Stowe and great for Sugarbush. The house has all you need for entertainment, comfort and amenities. We especially liked the fast drip, commercial coffee maker! The hot tub was also a hit after skiing each day. Good communication, well maintained and plenty of room. "
4 Mi to Sugarbush Resort: Waitsfield Retreat

Lake Champlain Estate. 25 Acres, 1500 Feet Lakefront, Beautiful View.

Lake Champlain Estate. 25 Acres, 1500 Feet Lakefront, Beautiful View.

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (115)
"The house fit our group of seven perfectly. Very close to the mountains. Hot tub and pool table "
Killington area home - 4-seasons & hot tub. Sleeps 12+
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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Other property types in Middlebury

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (7)
"Owners were very friendly and had everything you could think of, including local trails, equipment to go out on the lake which was included with the cabin games, local eats, etc."
The price is AED 531
AED 681 total
includes taxes & fees
24 Feb - 25 Feb
Trout House Village Resort

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (184)
"The cabin was pristine. The pond and surrounding woodland are breathtaking. Loved the drive in from the main road..so beautiful in the winter. A well needed reprieve from the daily grind. I would love to stay again in the summer months."
The price is AED 514
AED 658 total
includes taxes & fees
25 Feb - 26 Feb
Ultimate relaxing vacation
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.