Chittenden Vacation Rentals

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Browse Select Chittenden Vacation Homes

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

9.4 out of 10, Exceptional, (105)
"My family has stayed here 2 weekends and it was perfect for us. Great location and perfect area to relax. Our dog enjoyed swimming and we enjoyed fishing. Great communication with manager also. Look forward to staying here again!"
Water front home with large two tiered deck! 2 bathrooms 😂

Killington Farmhouse-Mountain Biking, Golf, Hiking

10.0 out of 10, Exceptional, (3)
"We visited in the summer…Spacious with room to spread out. Clean with all the things you need. Good communication. Laundry area a little spooky but great working laundry area."
Killington Farmhouse-Mountain Biking, Golf, Hiking

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

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (59)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Recently updated home with shared hot tub, pool, and easy ski access

8.4 out of 10, Very good, (42)
"Great place"
Recently updated home with shared hot tub, pool, and easy ski access

Premier Woodstock Village Riverfront Home

Premier Woodstock Village Riverfront Home

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (46)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

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

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
The price is CA $115
CA $412 total
includes taxes & fees
Aug 11 - Aug 12
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

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

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (218)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

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

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is CA $143
CA $216 total
includes taxes & fees
Aug 25 - Aug 26
104 Two Queen Bed Standard Hotel Room outdoor heated pool

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is CA $129
CA $195 total
includes taxes & fees
Aug 20 - Aug 21
Sleep Woodstock - 2 Double Beds - Dog Friendly

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (37)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

9.8 out of 10, Exceptional, (47)
"Couldn’t ask for much more than this property. Perfect location near Sugar Bush, big beautiful hot tub and wood fireplace to relax by at the end of the night. Blend that with a huge kitchen to cook in and basement / rec room for the kids to call their own and it created an environment for the perfect week. Great location, great communication all around. "
Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont

The price is CA $227
CA $702 total
includes taxes & fees
Aug 10 - Aug 11
The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
The price is CA $272
CA $832 total
includes taxes & fees
Aug 10 - Aug 11
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

Valley View Retreat is a tastefully decorated home. Beautiful views

10.0 out of 10, Exceptional, (2)
"The home was so comfortable and had a gorgeous view of the mountains. It was so convenient to the ski slopes. Our family of 4 really enjoyed our stay."
Valley View Retreat is a tastefully decorated home. Beautiful 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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Top Chittenden Hotel Reviews