Holiday rentals in Chittenden

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

WilliamRating, 5 stars2 months ago

The place was perfect for our winter family vacation. The home was as described in a beautiful setting with a great view. If staying in the winter months having a vehicle with at least all wheel drive is helpful, as this is Vermont. The home is out of the way, but easy driving distance to ski and explore the nearby towns.

5 out of 5 average rating, 5 reviews

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

SeanRating, 5 stars2 months ago

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

4.97 out of 5 average rating, 30 reviews

Cabin in Killington

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

JakeRating, 5 stars1 month ago

Sadie’s ski house was fantastic! It had everything we needed for a group of five adults and a child, and was only a short walk to a ski trail (great eastern). Check in/out was very easy. I’d be happy to stay again!

4.93 out of 5 average rating, 139 reviews

Home in Whitehall

Lakefront A-Frame Home Emerald Lake, NY

MelissaRating, 5 stars6 months ago

Beautiful home! Went at the peak of fall and the view of the lake and the changing leaves from all of the main rooms in the home was so perfect and cozy. The house had all of the items you need for a great stay. We absolutely loved fishing on the lake, the fire pit in the backyard and cozying up on the couches to watch a movie at night. We will definitely be coming back!

5 out of 5 average rating, 4 reviews

Home in Pomfret

Next to Saskadena Ski, Great Views | Half Past Six

AutumnRating, 5 stars2 months ago

Family of five on a northeast road trip enjoyed a rather cold but very beautiful snowy few days in this home that clearly has been loved by many for many, many years. We enjoyed being a part of the history. Kids had fun in the snow exploring the backyard. Plenty of space and beautiful views. Only downside was not being able to use the fireplaces!

5 out of 5 average rating, 59 reviews

Chalet in Mount Holly

Cozy chalet mins from Okemo & VAST.

RogerRating, 5 stars2 months ago

Had a great midweek family ski vaca and the house was perfect for our needs. Close proximity to Okemo and town. The house had lots of room to spread out, and the kitchen was fully equipped. Would definitely look to stay here again.

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Stay near Chittenden's top sights

Pico Mountain Ski Resort100 locals recommend

Deer Leap Trail40 locals recommend

Green Mountain National Golf Course35 locals recommend

Mountain Top Inn & Resort32 locals recommend

Clear River Tavern23 locals recommend

Gifford Woods State Park20 locals recommend

Other great holiday rentals in Chittenden

5 out of 5 average rating, 12 reviews

Home in Wells

Breathtaking Lakeside Retreat!

BrianRating, 5 stars2 months ago

Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

4.85 out of 5 average rating, 249 reviews

Cabin in Mendon

THE CABIN....a Vermont log home

JeffRating, 5 stars1 month ago

Bill's cabin was excellent. Rustic and rural but close to Killington and Pico, and a quick ride to Rutland. It was clean, comfy and had all we needed for a great little stay. It got a thumbs up from my wife and that is a high standard to meet. She even liked the king bed so much she was looking for the label to get one like it for home. I'm a guy and don't need much. The cabin made me feel like I was staying at a friend's house. You can nit-pick about the lighting and other minor stuff, but to me this place was a 10 out of 10 stars. We may be back next year for a longer ski vacation. Thanks Bill.

4.75 out of 5 average rating, 92 reviews

Apartment in Killington

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago

Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

4.84 out of 5 average rating, 88 reviews

Home in Killington

Killington Racquetball House

EmersynRating, 5 stars3 weeks ago

This was our second time staying at the racquetball house and it was just as incredible as the first. Lucked out with some great spring skiing on Friday, and checked into the Airbnb after. The house is very conveniently located to the mountain. We made full use of the court. Played racquetball, volleyball, dodgeball, kickball, pickleball, wall ball. Basically just spent all weekend playing games in the court and then relaxing in the hot tub to end the day. The living room / kitchen area is a great gathering layout. We will definitely be back.

4.81 out of 5 average rating, 89 reviews

Chalet in Granville

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars6 months ago

My wife and I thoroughly enjoyed our stay at John's Chalet. The house was exactly as described beautiful inside and out. We loved seeing all the wildlife around the home every day. The home is very private and close to many outdoor activities especially hiking. We would certainly consider this home again on our next trip to Vermont. Sincerely Paul & Rebecca

5 out of 5 average rating, 55 reviews

Home in Chittenden

Gigi and Pops' Secret Cabin

LaurenRating, 5 stars4 weeks ago

Wow! What a spot! Not only is the house amazing, the property is also amazing! The location is 10 min from town and 10 minutes to the mountain! The house was very clean and the owners thought of everything that you would need! We brought our 4 young kids and between the fort outside and the playroom, they had the best time! We will definitely be back!

5 out of 5 average rating, 8 reviews

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago

I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!