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Compare 217 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

9.6 out of 10, Exceptional, (41)
"Amazing view from the back deck, very clean home, plenty of room for our family of 6. Will definitely be staying here again next time we're in Lake George!"
Gorgeous lakeview retreat with wraparound porch, wood stove, & WiFi - dogs OK

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

10.0 out of 10, Exceptional, (172)
"Barb was an absolutely lovely host, who was easy to get ahold of if need be. The property's views are absolutely incredible. You have everything you need to just have a relaxing vacation with your pup & spouse ! "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

Luxurious guest home with private art gallery in the heart of a historic village

10.0 out of 10, Exceptional, (13)
"Absolutely unique and amazing experience staying here. Space is gorgeously appointed and impeccably clean. Walk out the door right into a cute town with all the amenities right there. Edward was the perfect host: attentive to detail, communicative and pleasant. We will definitely stay here again if in the area! "
Luxurious guest home with private art gallery in the heart of a historic village

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (41)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

Large multi-family ski home located on the slopes of Sugarbush Resort

10.0 out of 10, Exceptional, (21)
"We had four couples coming from four different states. Our stay was during the end of September 2024. This house has ample room both in bedrooms and living space. Super views even with leaves on the trees. We would return to this house."
Large multi-family ski home located on the slopes of Sugarbush Resort

The Brandon Inn - King Room

8.4 out of 10, Very Good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is SAR 582
SAR 744 total
includes taxes & fees
24 Nov - 25 Nov
The Brandon Inn - King Room

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"This place is a nice, cozy little getaway. Great location!! Host has thought of every little accoutrement one might need when you're away from home, everything from hand lotion to a French press!! This was my second stay here, definitely won't be my last!! Love it!"
The price is SAR 300
SAR 458 total
includes taxes & fees
24 Nov - 25 Nov
Cozy Private Bedroom with Own Entrance - No Shower

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

10.0 out of 10, Exceptional, (3)
Dog-friendly home near Lake George with deck, grill, media room, fireplace, W/D

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

2.0 star property
10.0 out of 10, Exceptional, (4)
Modern farmhouse in classic VT orchard setting - stunning sunsets & location

Cozy A-frame with loft, deck and easy ski access

7.6 out of 10, Good, (7)
"The property had plenty of space for our group. I would suggest some steps be put in and some more care be spent on snow removal but we had fun sliding downhill to the entrance."
The price is SAR 345
SAR 1,885 total
includes taxes & fees
24 Nov - 25 Nov
Cozy A-frame with loft, deck and easy ski access

Light-filled retreat in Mad River Valley with internet & deck

10.0 out of 10, Exceptional, (2)
"This home is the perfect place to escape the busy lifestyle of every day life. To relax and reset."
The price is SAR 612
SAR 2,062 total
includes taxes & fees
24 Nov - 25 Nov
Light-filled retreat in Mad River Valley with internet & deck

Classic Vermont Farmhouse near Sugarbush Resort

9.8 out of 10, Exceptional, (32)
"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

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (68)
"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 Brandon Inn - Family Suite For Four

10.0 out of 10, Exceptional, (1)
"Very charming historic inn. Suite was perfect for our family of four. We all liked the historic elevator! The bar looked very nice and hopefully it will be open more consistently. The town had several good restaurants. We would stay here again for sure!"
The price is SAR 732
SAR 936 total
includes taxes & fees
24 Nov - 25 Nov
The Brandon Inn - Family Suite For Four

Beautiful Family Home Central to Mad River Valley

10.0 out of 10, Exceptional, (3)
"We had a great time at the Mad River Valley house. The location was perfect for our scheduled ride at the Icelandic Horse Farm and we had a wonderful dinner around the corner at the 1824 House. We found lots of places in the area to hike with the dogs and the shopping in Waitsfield was also a pleasure. Overall it was a perfect long weekend."
The price is SAR 647
SAR 2,498 total
includes taxes & fees
26 Nov - 27 Nov
Beautiful Family Home Central to Mad River Valley

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

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

9.2 out of 10, Wonderful, (113)
"Check-in and communication with the Host was terrific up to and during our stay. The views from this home always took our breath away. Fully stocked kitchen khiels"
Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

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

9.6 out of 10, Exceptional, (27)
"Absolutely perfect for our early 20s children on a ski weekend with us. Proximity to Mad River Glen cannot be beat. Great set up with bedrooms and kitchen is perfect and we loved the great room set up."
Dog-friendly mountain home w/wood stove, deck, firepit, grill, washer/dryer

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

9.8 out of 10, Exceptional, (38)
"We had a wonderful visit to this house during peak fall foliage. It has great views of Mad River Valley and the Mad River ski area. You can walk to hiking trail access points. The property is private and serene, but also just a quick drive to Waitsfield. Plenty of seating in living room and for dining four group of 8. Nice, large entryway to keep gear in. Hot tub was wonderful. Our group of friends likes to cook and we really appreciated the fully stocked kitchen and grill. All the appliances,...
Ski home in the woods with a private hot tub & mountain views

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

9.8 out of 10, Exceptional, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
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

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (41)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
Cozy Loft for two with Hot Tub
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.