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Compare 225 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (42)
"This adorable house was just right for what my family needed. The location was perfect as well- quiet and with easy access to nearby town and walking trails. We very much appreciated how the bedrooms offered plenty of privacy and the shared spaces were very nice as well— I can highly recommend! "
Beautiful 4-Bedroom Home beside Middlebury College

Lake George Waterfront with Dock Space, fire pit and game room!

10.0 out of 10, Exceptional, (16)
"The host thought through all of the details! - hair dryers in the bathrooms, bath products, kitchen appliances, games, coffee selection, Wi-Fi , kayaks, life jackets - guaranteed a fun vacation. Plus, she is immediately responsive to all questions. Home and waterfront layout are perfect. Look no further. You want to stay here!"
Lake George Waterfront with Dock Space, fire pit and game room!

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

10.0 out of 10, Exceptional, (174)
"We had a great trip here. The view was beautiful and the amenities were amazing. Great for a weekend getaway. We look forward to returning in the future. Thank you Barb for the hospitality! "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

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

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 657
SAR 837 total
includes taxes & fees
24 Dec - 25 Dec
The Brandon Inn - King Room

Mountain Top - Fresh Pond - Killington - Hot Tub

9.8 out of 10, Exceptional, (6)
"This property was exactly as advertised. Plenty of space for everyone to hangout and have privacy when needed. It is a quick 20 minute drive to Killington. We would definitely rent it again!"
Mountain Top - Fresh Pond - Killington - Hot Tub

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

10.0 out of 10, Exceptional, (22)
"Our family stayed at Evan's home because we were attending a wedding (conveniently up the road) at Mountain Top Resort. The home gushes with Vermont charm! It was beautifully and thoughtfully decorated which made our stay so cozy. Evan thought of everything- from exact GPS directions, to helpful notes around the home to help his guests be comfortable! Evan was very helpful at every stage of our stay! We would absolutely 100% recommend staying at Evan's beautiful home!"
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

Secluded Vermont Home with Stunning Private View! Prime Location!

10.0 out of 10, Exceptional, (11)
"Beautiful house and great views, serene and relaxing."
Secluded Vermont Home with Stunning Private View! Prime Location!

Green Mountain Village Getaway in picturesque Bristol, Vermont.

3.5 star property
10.0 out of 10, Exceptional, (1)
"I stayed here with three friends for a weekend getaway. The house is roomy and clean. Bristol has a cute little downtown that is very walk-able from this location. We did one day of skiing at Sugarbush which was about a 35 minute drive in bad weather, so would be even quicker with clear skies. One of the reasons we selected this house was the outdoor hot tub and it did not disappoint! Troy was a great, available host. This place comes as advertised and was perfect for our little weekend...
Green Mountain Village Getaway in picturesque Bristol, Vermont.

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Lakeside Lodge at Fern Lake: 3BR/1BA Waterfront w/ Dock

Charming Ticonderoga Home - Walk to Downtown!

2.0 star property
9.6 out of 10, Exceptional, (4)
"I stayed here with my sisters and our husbands to attend a wedding at The Barn at Lord Howe... The house was absolutely beautiful and met our needs perfectly. Located a mere 4 minute drive from the venue, the house was fully equipped and Evolve was phenomenal to work with during our stay. They provided tons of information on all the local sites and things to do in the area! Highly recommend!"
Charming Ticonderoga Home - Walk to Downtown!

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, (114)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 12+

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

Beautiful Private Vermont Home 2 minutes to Sugarbush Resort at Mt. Ellen with views of the slopes

10.0 out of 10, Exceptional, (14)
"Excellent home for a family getaway. Clean and as described in listing. Great communication with rental management when needed. Close to swimming and downtown Waitsfield. Drivable to Burlington, Waterbury and Stowe for day trips. Would definitely book again for our family!!!"
Beautiful Private Vermont Home 2 minutes to Sugarbush Resort at Mt. Ellen with views of the slopes

Hague Vacation Rental ~ 2 Mi to Lake George!

7.2 out of 10, Good, (5)
"Located conveniently close to Rogers Rock State Park with boat inspection station and launch. This is a no-frills property which was quiet and clean, providing a pleasant stay. The driveway is steep and somewhat tight, but I was able to park a Ram pickup with 8ft bed and boat trailer without much trouble. I enjoyed the lack of cell service and WiFi - it was GREAT. It did smell somewhat like pets upon first entering, as it was a very humid day. we moved the dog bed downstairs and aired the...
Hague Vacation Rental ~ 2 Mi to Lake George!

4 Mi to Sugarbush Resort: Waitsfield Retreat

9.2 out of 10, Wonderful, (45)
"Nice homey location. Great for a large group! "
4 Mi to Sugarbush Resort: Waitsfield Retreat

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!

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

9.8 out of 10, Exceptional, (18)
"My husband and I enjoyed our stay with beautiful views and off the beaten path. We were comfortable in the space and looked forward to coming back each evening after a day of exploring. Wifi worked well. Host left a helpful binder with information and recommendations. We used the kitchen, and it had the cookware we needed."
Historic home on 1 acre with snowmobile trails in backyard & mountain views

Sugarbush Vista - 4000sq. ft. Vermont Estate with Stunning Mountain Views!

10.0 out of 10, Exceptional, (8)
"We needed a big home for our group of 9 old friends. This home was perfect for us. The property description and photos were accurate. Big windows looking out at a great view, with a nice deck too. Dining room table plenty big for all of us. Lots of room to spread out on the main floor, like when someone wanted to watch TV they could, not bothering the others. The bedrooms were very comfortable. The WiFi worked very well. The property setting was private. Its location was close enough to the...
Sugarbush Vista - 4000sq. ft. Vermont Estate with Stunning Mountain 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.
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Other property types in Middlebury

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (134)
"Cabin had everything we needed and more. We found it to be a great location for the small day trips we did to surrounding towns. Location is just gorgeous. "
The price is SAR 902
SAR 1,754 total
includes taxes & fees
6 Jan - 7 January 2025
Stetson Hollow Cabin by Stetson Brook

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (178)
"We had a lovely time, and Dan was very accommodating, especially when we had to delay our trip by a day due to a snow storm!"
The price is SAR 526
SAR 673 total
includes taxes & fees
6 Jan - 7 January 2025
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.