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Compare 515 Vacation Homes in Chittenden with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres

9.8 out of 10, Exceptional, (25)
"We stayed at the house for a family wedding. It was a perfect place for our family. "
Spacious country home, beautiful sunsets, 40 acres

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (93)
"My wife, adult daughter and my wife's parents planned this trip for several months for a leaf tour outside of our home state of PA. We never have visited VT. But have tons of friends that have and recommended a few spots. We wanted to find a spot that would accommodate our 80+ year old parents and their walking limitations and allow us the opportunity to comfortably stay in for the night should we need a break . The location provided a great home-base for our meandering around the state. ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (108)
"Great home, abundant firewood, lighting far better than the usual VRBO, lots of cookware, and kind owner. We had an excellent time!"
Spectacular 4 Bed Killington Home

Slopeside Chalet - Ski to and from your home!

10.0 out of 10, Exceptional, (9)
"Exceeded my expectations - luxury bedding - condo felt homey and just smelled good! Hosts very responsive! Best Topridge experience we’ve had"
The price is AED 1,166
AED 3,115 total
includes taxes & fees
2 Dec - 3 Dec
Slopeside Chalet - Ski to and from your home!

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

9.8 out of 10, Exceptional, (52)
"This is our second stay at Joel’s condo. His improvements to the lower floor are very nice and made a lot of sense. We enjoyed the location and condo once again. Joel continues to be very thoughtful and helpful. A great place to get away, relax, and have fun. We also got some late season skiing in for those of us who enjoy the slopes."
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

9.2 out of 10, Wonderful, (65)
"Best place to visit for fall leaf peeping! Very enjoyable experience "
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

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

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

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 AED 569
AED 724 total
includes taxes & fees
26 Nov - 27 Nov
The Brandon Inn - King Room

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (63)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

10.0 out of 10, Exceptional, (54)
"Beautiful fall foliage trip, Woodsy, cozy, private mountain getaway, close to everything house was well located, private, pleasant, well appointed and tastefully decorated, stunning views out the back. Beds and couches very comfortable!!! Hot tub works well. Good vibes overall. we were a party of 2 adults and 2 kids, couldve had 2 more people comfortably, but more than that would have been too much."
Private Mountain View minutes to Hiking, biking, golfing, skiing, snowboarding

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 AED 294
AED 448 total
includes taxes & fees
26 Nov - 27 Nov
Cozy Private Bedroom with Own Entrance - No Shower

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (74)
"This is my third stay here. It's a wonderful cabin and property for nature lovers! The lovely deck is a perfect place to take in the surroundings. A pond, a waterfall, a fire pit and a cozy cabin, totally private, what more could you ask for? If you have physical limitations, just be aware that you have to walk up a small hill and some stairs from the parking area and the spiral staircase inside may be difficult to navigate for some. "
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Spacious 3-story home near ski area with private hot tub, Ping-Pong

6.8 out of 10, (14)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

9.0 out of 10, Wonderful, (78)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

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

The Racquetball House - Home to the BIGGEST hot tub in Killington!

9.6 out of 10, Exceptional, (62)
"This was a great house for a group of friends to spend a wonderful weekend exploring the area. Very quiet and private - the house is huge and the rooms were very nice. It was very comfortable and the younger folks loved the raquetball court. Owners were easy to work with and had instructions for everything. Highly recommend"
The Racquetball House - Home to the BIGGEST hot tub in Killington!

HappyCub! Hot tub, game room, fire pit!

10.0 out of 10, Exceptional, (14)
"We had a great stay at the Happy Cub! Comfortable, clean and spacious for our group. The hosts were very communicative in order to assure our check-in and stay were smooth and we could enjoy our get away. Thank you!"
The price is AED 948
AED 2,418 total
includes taxes & fees
2 Dec - 3 Dec
HappyCub! Hot tub, game room, fire pit!

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
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 Chittenden

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

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.