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

Incredible Family Getaway Home With Boat Dock

10.0 out of 10, Exceptional, (134)
"Wonderful home with a great view. Would love to stay here again!"
Incredible Family Getaway Home With Boat Dock

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"Very comfortable stay. "
The price is AED 294
AED 448 total
includes taxes & fees
6 May - 7 May
Cozy Private Bedroom with Own Entrance - No Shower

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

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

10.0 out of 10, Exceptional, (181)
"Absolutely perfect location for what we were looking for! Beautiful view of the Lake Champlain and the house was perfect and comfortable- it had everything we needed! Peaceful and relaxing right before Christmas. "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

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

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

9.8 out of 10, Exceptional, (43)
"We had a wonderful time staying here. The house is warm and cozy with stunning views of the mountains. The house is well kept, clean, with up to date appliances and fixtures. We would stay here again. "
Ski home in the woods with a private hot tub & mountain views

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!

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

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

1 Mi to Sugarbush Resort: Dog-Friendly Home!

9.0 out of 10, Wonderful, (2)
"We had a fantastic stay at this rental! The house was spotless, with an updated, well-stocked kitchen that made cooking easy and enjoyable. There's plenty of space, making it perfect for a large group or multiple families. It’s both modern and cozy, with a great layout for relaxing and spending time together. The deck and fire pit area were a big hit in the evenings. The location is ideal—just minutes from skiing and close to town for shopping and dining. The host was incredibly responsive and...
1 Mi to Sugarbush Resort: Dog-Friendly Home!

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (14)
"The owners were wonderful and very responsive. We enjoyed our stay - beautiful location and view. The home was extremely inviting and perfect for our needs! "
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

Whispering Pines & Game Nights

8.0 out of 10, Very Good, (1)
Whispering Pines & Game Nights

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

10.0 out of 10, Exceptional, (22)
"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

Stunning Modern Retreat Overlooking The Mad River

10.0 out of 10, Exceptional, (8)
"Wonderful modern and upscale rental property with amazing views of the mad river. Absolutely lovely!"
The price is AED 617
AED 2,489 total
includes taxes & fees
14 May - 15 May
Stunning Modern Retreat Overlooking The Mad River

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

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (73)
"Great place to stay and great host!"
The price is AED 367
AED 1,160 total
includes taxes & fees
6 May - 7 May
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

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

Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer

9.6 out of 10, Exceptional, (29)
"We loved our stay - the location is great and there was plenty of space for 4 adults and 4 kids. For the price we were paying, we were expecting a more updated space."
Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer

4 Mi to Sugarbush Resort: Waitsfield Retreat

9.2 out of 10, Wonderful, (47)
"Nice homey location. Great for a large group! "
4 Mi to Sugarbush Resort: Waitsfield Retreat

Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D

8.8 out of 10, Excellent, (6)
"Loved loved loved this house. It was clean, spacious, beautiful and best of all pet friendly."
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D
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

Beautiful brand new 1-bedroom apt with gorgeous views

10.0 out of 10, Exceptional, (43)
"We enjoyed our visit very much!"
Beautiful brand new 1-bedroom apt with gorgeous views

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is AED 531
AED 681 total
includes taxes & fees
6 May - 7 May
Trout House Village Resort

Lake George Water Front Cabin Spectacular Views

9.6 out of 10, Exceptional, (30)
"The house was perfect for my family! The teens loved kayaking! The view was absolutely stunning! Wish we could have stayed longer! Will stay again next year!"
The price is AED 2,020
AED 4,191 total
includes taxes & fees
6 May - 7 May
Lake George Water Front Cabin Spectacular 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.