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Compare 501 Vacation Homes in Chittenden with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (21)
"Hosts are excellent communicators, and property is accurately described. When I arrived, there was an alarm going off on the stovetop. I didn’t want to bother the host, but I did reach out the following morning, and within minutes, I received a response which immediately solved the problem (reset breaker). This provides an excellent location to visit life-long friends in the area, with the convenience of a great kitchen. (We are already quite familiar with the surrounding area.) The...
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, (90)
"We had a great stay at this property, it had everything we needed for our family of 5 for several weeks of temporary living. Comfortable and quiet space and close enough to stores, etc. "
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
4 Season Secluded Lakefront Home near Ski Mountains
9.4 out of 10, Exceptional, (61)
"This is now on our top 10 vacation lists. It is an outstanding location. The water quality is great, and there's a perfect little beach for the very little people. The house is rustic but has everything one might need. The variety of boats allowed us to see around the lake. We hated to leave."
4 Season Secluded Lakefront Home near Ski Mountains
Slopeside Chalet - Ski to and from your home!
10.0 out of 10, Exceptional, (7)
"Views are incredible! Already thinking of rebooking! Thank you "
The price is $713
includes taxes & fees
$647 per night
Sep 29 - Sep 30
Slopeside Chalet - Ski to and from your home!
Blueberry Hill Escape Pet Friendly HotTub Fire pit
9.8 out of 10, Exceptional, (12)
"On arrival I loved the breathtaking views of the mountains ! The house was so spacious. Each kid had their own room and my husband and I loved having a master suite ! Our dog was so comfortable there as well ! I am really big on cleanliness and this house was immaculate !! We loved the hot tub! So relaxing ! I walked the dog around the house every morning and had noticed fruit trees ! The peaches were delicious ! Got Home from dinner one night amd we were getting of the car and a black bear...
The price is $586
includes taxes & fees
$530 per night
Sep 30 - Oct 1
Blueberry Hill Escape Pet Friendly HotTub Fire pit
Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen
10.0 out of 10, Exceptional, (34)
"This waterfront, sandy bottom, lakefront home is truly amazing!! The home itself is equipped with everything you could want or need. It is so comfortable. You never feel on top of each other. The open concept is perfect. The lake views are beautiful. We were in the water everyday. Kayaking, paddleboarding, and just floating around. Craig is an amazing host. So quick to answer any questions. This is our favorite vacation home and we can't wait for next summer!"
Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen
Cozy private country setting - 15 miles from Woodstock
10.0 out of 10, Exceptional, (20)
"A lovely spot to stay! Great communication with the host!"
Cozy private country setting - 15 miles from Woodstock
Idyllic Wallingford Retreat - Near Skiing & Hiking
9.8 out of 10, Exceptional, (14)
"Nice loft. Had everything we needed. It had lots of little extras. Everything was very clean with only an exception of a pan that the previous guest had not washed completely. Overall it was very nice."
Idyllic Wallingford Retreat - Near Skiing & Hiking
Historic Schoolhouse in Rural Vermont Beauty Spot
10.0 out of 10, Exceptional, (24)
"The schoolhouse was just what we were looking for- a quiet country location with good walking, hiking, exploring, and close to Randolph. We appreciated the ephemera- books, maps, newspapers. Looking through the shelves and cabinets was an adventure unto itself. We spend time outdoors so one plus would have been more comfortable outdoor furniture. Thank you, Terrie, we have a terrific time!"
Historic Schoolhouse in Rural Vermont Beauty Spot
Luxurious guest home with private art gallery in the heart of a historic village
10.0 out of 10, Exceptional, (9)
"Beautiful property! Walking distance to shops and restaurants in Brandon."
The price is $450
includes taxes & fees
$398 per night
Sep 29 - Sep 30
Luxurious guest home with private art gallery in the heart of a historic village
Spacious 3-story home near ski area with private hot tub, Ping-Pong
6.8 out of 10, (13)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong
Beautiful 4-Bedroom Home beside Middlebury College
9.6 out of 10, Exceptional, (38)
"We loved our time at this beautiful home. A quaint cottage feel with a beautiful English garden in the back. A short field walk to Middlebury College and just minutes from downtown."
Beautiful 4-Bedroom Home beside Middlebury College
The Brandon Inn - Fourth Floor Queen Room
9.4 out of 10, Exceptional, (3)
"This is a great spot. Was in town w Gus my field spaniel and we had a nice time at the Inn. The room was a bit antiquated but that’s part of the charm. We hiked the green mountains/silver lake trail and this place was perfect to rest weary bones. The rates are very reasonable and the property is quite beautiful. Will be back! "
The price is $185
includes taxes & fees
$170 per night
Oct 20 - Oct 21
The Brandon Inn - Fourth Floor Queen Room
Merry Maple Getaway
9.6 out of 10, Exceptional, (16)
"Great property for a ski trip!!! Location is perfect to hit multiple resorts. The house was clean and exactly what was expected per the listing."
Merry Maple Getaway
Lovely Brookfield Home w/Private Deck & Views
10.0 out of 10, Exceptional, (16)
"My family stayed at Winderlea for 2 nights to attend a family party. This house was absolutely perfect for us! There was so much space & privacy and many places to gather. The house was beautiful and fully equipped with everything we needed. I honestly can't say one negative thing. The property surrounding the home was gorgeous and peaceful. Brian greeted us at the property and was so nice. We give it ☆☆☆☆☆!! furnished and "
Lovely Brookfield Home w/Private Deck & Views
Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!
10.0 out of 10, Exceptional, (22)
"Perfect accommodations for our family of 5! Easy drive into Killington for skiing. House had all the things we needed and communication with the host was prompt and responsive."
Cozy Home, Minutes from Killington! Washer/Dryer & Free Disney+/Peacock!
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!
7.0 out of 10, Good, (2)
"This rental was not only clean and roomy but in a great spot. It was spacious throughout and the beds were comfortable. The backyard and hot tub were very nice too.. I would definitely stay again!"
Mendon Home w/ Hot Tub, Fire Pit & Near Skiing!
Beechwood - 4 Bedrooms and 3 Baths, sleeps 10
10.0 out of 10, Exceptional, (1)
"We loved our stay here. Only 18 minutes from killington. The house was clean and cozy. I’d definitely book again."
Beechwood - 4 Bedrooms and 3 Baths, sleeps 10
Ski Retreat Townhome in Plymouth, VT
9.0 out of 10, Wonderful, (4)
"Beautiful views in a very private, peaceful location Not as close to Killington as we thought and a little out of the way of your looking for restaurants or quick bite to eat. Clean and large enough for family of 5. TV is on the smaller side for size of living room area and no streaming service avail if that’s important. Also would’ve been nice to have a working fireplace,gas or otherwise. Overall fine place to stay for the value."
Ski Retreat Townhome in Plymouth, VT
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
9.8 out of 10, Exceptional, (19)
"If you are looking for a great place to stay near Killington/Bridgewaters this is the spot! Clean, neat and comfortable! We will be back next year! thanks!"
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
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Other property types in Chittenden

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (463)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"Jeff is a very gracious host and kept in communication throughout this VRBO experience. The cabin is a wonderfully enchanting place with a lot of privacy, and everything you need to make your time spent there a very relaxing and rewarding experience. The cabin is within 20 minutes of Stowe, Vt. The culture is downhome and the food is great!!!!"
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.