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Compare 507 Vacation Homes in Chittenden with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres
Brand new chef's kitchen
Spacious country home, beautiful sunsets, 40 acres
9.8 out of 10, Exceptional, (24)
"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
Living area
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
Exterior
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!
Enjoy the views of Bear Mountain directly from the hot tub!
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 SAR 791
SAR 2,675 total
includes taxes & fees
6 Nov - 7 Nov
Slopeside Chalet - Ski to and from your home!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Image from trailhead
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
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
The Gallery at Six, circa 1880
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
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
Front view from street.
Beautiful 4-Bedroom Home beside Middlebury College
9.6 out of 10, Exceptional, (40)
"We so enjoyed our stay in this beautiful home. It has been so well cared for an exudes the love and memories of the owners. As a family of eight seniors, we appreciated the warmth and comfort of the home. It is exactly as pictured. Communication with the property owner and the property manager was always friendly and prompt. We would love to come again. "
Beautiful 4-Bedroom Home beside Middlebury College
The Brandon Inn - King Room
Exterior
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 740 total
includes taxes & fees
6 Nov - 7 Nov
The Brandon Inn - King Room
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior
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
beautiful fall day at house view from deck
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
Room
Cozy Private Bedroom with Own Entrance - No Shower
10.0 out of 10, Exceptional, (2)
"Super quiet for being attatched to a lived in house. Love the fact it was in town but very private. Easy check in! "
The price is SAR 300
SAR 458 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Private Bedroom with Own Entrance - No Shower
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
2.0 star property
10.0 out of 10, Exceptional, (68)
"The property is beautiful and very quiet. There are a few steps to go up to the cabin from the parking, it's a little steep but nothing too intense (probably more challenging with snow?). There is a little pond with a turtle and small fish where the waterfall drops. The cabin itself is beautiful and modern on the inside, a cozy living room, a tv room (Roku with some cable), a large patio in the front, the stairs are a little small but solid, the rooms are not huge and there is the slopped...
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Spacious 3-story home near ski area with private hot tub, Ping-Pong
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
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
Aerial view of the property
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!
View of house from top of driveway.
The Racquetball House - Home to the BIGGEST hot tub in Killington!
9.6 out of 10, Exceptional, (62)
"Perfect location and size house for our event weekend with friends. Would go back and recommend! "
The Racquetball House - Home to the BIGGEST hot tub in Killington!
HappyCub! Hot tub, game room, fire pit!
Sink into our inviting living room, where laughter begins and memories are made.
HappyCub! Hot tub, game room, fire pit!
10.0 out of 10, Exceptional, (13)
"We were so happy with our stay here! There were thoughtful personalized touches, the space was beautiful and had everything we needed, and location was great for what we were looking for. Thank you for the great stay! "
The price is SAR 726
SAR 2,164 total
includes taxes & fees
7 Nov - 8 Nov
HappyCub! Hot tub, game room, fire pit!
Middlebury Gem open concept and 5 minutes from town
Exterior detail
Middlebury Gem open concept and 5 minutes from town
10.0 out of 10, Exceptional, (66)
"Our family spent the weekend at this property for a wedding in Bridport. It was very clean, very well stocked and very comfortable for all 6 of us. Close to all stores, markets, restaurants and the Main street in Middlebury. Highly recommend this rental. "
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

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (469)
"We wouldn't change a thing about our trip. It was, by far, the best place we have been to. The accommodations were cozy and everything you may possibly need was there for you! The large projector TV screen was a definitely welcomed bonus along with the hot tub! It was very quiet and secluded...Loved everything ❤️ In addition, if there is concern about Verizon service, Verizon 'Wi-Fi calling' worked for every phone call every time in the cabin. Jeff was a very considerate host and contacted us...
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
9.0 out of 10, Wonderful, (18)
"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.