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Compare 684 Vacation Homes in Chittenden with updated reviews, rates, and availability.

Spacious country home, beautiful sunsets, 40 acres

10.0 out of 10, Exceptional, (32)
"Awsome place to stay for a week! "
The price is AED 533
AED 1,831 total
includes taxes & fees
1 Jun - 2 Jun
Spacious country home, beautiful sunsets, 40 acres

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (22)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (101)
"Perfect place to just get away for a few days and relax/unwind. Absolutely beautiful views and friendly neighborhood. Downtown was a convenient drive and Rutland is a short drive away for more choices to eat out. Truly enjoyed our stay!"
Water front home with large two tiered deck! 2 bathrooms 😂

Cottage on east side of Lake Bomoseen, on-site boat slip included

9.0 out of 10, Wonderful, (8)
"We enjoyed out stay here and will be coming back."
Cottage on east side of Lake Bomoseen, on-site boat slip included

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

9.4 out of 10, Exceptional, (26)
"The property and home was exactly as listed. Beautiful view of the lake from the main sitting room. The home was very clean and comfortable. Everything we needed for our stay was provided."
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Off Grid Glamping Shed with River Access

2.0 star property
The price is AED 239
AED 370 total
includes taxes & fees
31 May - 1 Jun
Off Grid Glamping Shed with River Access

Muwu in Killington Area with Jacuzzi

The price is AED 1,010
AED 1,888 total
includes taxes & fees
2 Jun - 3 Jun
Muwu in Killington Area with Jacuzzi

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (6)
"A true gem."
BRIDGEWATER RETREAT

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (49)
"I can’t thank Susannah enough for the warm welcome, sparkling clean property, and easy check in/out process. Highly recommend this stay!!!! "
Beautiful 4-Bedroom Home beside Middlebury College

Cute, Renovated Historic Home on River, Walk to Downtown

9.6 out of 10, Exceptional, (9)
"I really enjoyed my month here in Brandon and 19 River. I would stay here again!"
Cute, Renovated Historic Home on River, Walk to Downtown

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Great place - very comfortable!!"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Downtown Middlebury River House

Downtown Middlebury River House

Family Retreat at Lake Bomoseen: Restored 1910s Home, 4BR/2BA

2.0 star property
Family Retreat at Lake Bomoseen: Restored 1910s Home, 4BR/2BA

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

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (71)
"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 Bomoseen Bungalow: Vermont Lake House with Private Dock

2.0 star property
The Bomoseen Bungalow: Vermont Lake House with Private Dock

Brand new Aframe btw Okemo and Killington with a dock on Lake Rescue

10.0 out of 10, Exceptional, (1)
"The house was fantastic, soft furnishings made us feel right at home. Pool room in the basement was great fun. Great location, peaceful, comfortable and immaculately maintained home. Owners were super responsive for any questions and made us feel at ease. Thank you!"
Brand new Aframe btw Okemo and Killington with a dock on Lake Rescue

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"My family of 8 stayed here for a ski vacation, and we loved it. Everything from the comfy beds, well equipped kitchen, space for ski equipment, and room for all of us to be together was perfect!! The hosts were Amazing! "
FiddleHead Lane-Near Killington, Fireplace, Grill

Killington ski house

9.4 out of 10, Exceptional, (35)
"Property owner was excellent! We enjoyed our stay."
Killington ski house
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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