Holiday Homes in Chittenden

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Featured Holiday Homes in Chittenden and around

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

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

9.4 out of 10, Exceptional, (13)
"We enjoyed out stay here and will be coming back."
Cottage on east side of Lake Bomoseen, on-site boat slip included

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

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

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

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (17)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"Beautiful house on an amazing piece of property. The house was very comfortable for two families of four. It has everything you could need and more. The hosts were very responsive. We will definitely stay here again."
New Listing - Luxury log home with stunning views

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

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

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

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

2.0 star property
9.8 out of 10, Exceptional, (76)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

10.0 out of 10, Exceptional, (41)
"Our granddaughter was getting married at Lake Bomoseen, only a short 3 or 4 minute ride from this beautiful house. We had our 4 grandchildren and their parents with us, this house let us spread out and have fun. We did not have good weather but that didn't stop my 8 year old granddaughter from jumping in the lake. We wish we could have enjoyed the outside more, but with a rainy weekend, we were so happy we had the expanse of this home. We played charades, games, made puzzles. This home has...
Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

Premier Woodstock Village Riverfront Home

Premier Woodstock Village Riverfront Home

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (84)
"Alex's house is a great place to stay for a weekend getaway! The peace and quiet coupled with surreal mountain views made for a memorable trip with friends. "
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

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, (63)
"The perfect place for our friends and family to stay!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

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

8.6 out of 10, Excellent, (27)
"Cool location, perfect basic ski house"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

10.0 out of 10, Exceptional, (48)
"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!!!

BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

Killington Home w/ Hot Tub, Mtn Views & Updates!

9.0 out of 10, Wonderful, (9)
"It was a great stay house is close to Everything you would need restaurants ski resort ect.. it was just all in all great stay no issues. Communication was spot on!"
Killington Home w/ Hot Tub, Mtn Views & Updates!

3BR w Incredible View, Hot Tub & Sauna

10.0 out of 10, Exceptional, (6)
"This house has everything - views, lots of space, comfortable beds, and a great location. "
3BR w Incredible View, Hot Tub & Sauna
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

Find out more about Chittenden

Find out more about Chittenden

Chittenden Holiday Homes information

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714 Holiday Homes
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