Holiday houses in Chittenden

4.99 out of 5 average rating, 107 reviews

Tiny home in Castleton

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

4.99 out of 5 average rating, 138 reviews

Apartment in Pittsford

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or young children.

4.93 out of 5 average rating, 107 reviews

Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

4.96 out of 5 average rating, 178 reviews

Tiny home in Pittsford

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

4.96 out of 5 average rating, 137 reviews

Yurt in Pittsford

Remote Cozy Yurt with Sunset Views

Enjoy some time in a secluded yurt nestled in a quiet valley with spectacular sunset views. It comfortably sleeps 4, but can accommodate more. There is a bathhouse with an outdoor shower, compost toilet, and sink. Complete with propane stovetop, grill, and all necessary kitchenware. Stays in colder months will enjoy the warmth and comfort of a wood stove. Guests can also enjoy a small trail system on property for exercise or leisure. We hope you will come enjoy this peaceful retreat!

4.98 out of 5 average rating, 157 reviews

Cabin in Pittsfield

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

4.96 out of 5 average rating, 126 reviews

Cabin in Chittenden

Cabin on The Hill

Relax with the whole family at this peaceful place. Private, cozy, clean, comfortable getaway in Chittenden Vermont. This beautiful cabin is off the grid with solar power and push button generator. Chittenden is a small drive to endless recreational activities for every season. It is the perfect rustic space for a couple or a small family. It is centrally located between Killington and Rutland. Everything you need is within a 20 to 30 minute drive.

4.95 out of 5 average rating, 474 reviews

Cabin in Rochester

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

4.86 out of 5 average rating, 184 reviews

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

4.96 out of 5 average rating, 609 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

4.95 out of 5 average rating, 111 reviews

Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

5 out of 5 average rating, 248 reviews

Apartment in Chittenden

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

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Other great holiday rentals in Chittenden

Superhost

Barn in Chittenden

5 out of 5 average rating, 3 reviews

Summer retreat in Mod Rural barn, Monthly Discount

AndresRating, 5 stars15 months ago

Karen was such a lovely host! She gave us very clear instruction on how to get inside, welcomed us when we arrived to make sure we had everything we needed, and was even nice enough to offer us a friendly gift! The house was well furnished, had a huge TV for entertainment, washer & dryer units, and plenty of kitchen cutlery and cookware for making meals. Location is close to killington, about ~20 minutes from the snowshed parking lot. It’s also close to groceries and dining. 10/10 had an incredible stay with Karen, I will definitely visit again!

4.93 out of 5 average rating, 28 reviews

Red Rooster Air BnB

LeifRating, 5 stars1 week ago

We enjoyed our stay here, very convenient location with lots of good food around. The place had all the amenities you would need for an extended stay.

4.93 out of 5 average rating, 27 reviews

Cabin in Rochester

The Creek Cabin at Sky Hollow

AnnaRating, 5 stars3 weeks ago

The stay was fantastic. The cabin is located in a perfect area surrounded by the woods, beautiful trails, a sauna and just so much greenery we couldn't believe it. The cabin itself was incredibly well put together, had everything you'd need and then some. Jess was very accommodating and answered every question we had. 100% recommend!

4.92 out of 5 average rating, 26 reviews

Home in Chittenden

Backyard Deck+Modern Interior | House on the Rocks

CatherineRating, 5 stars2 months ago

Our group of 10 (8 adults + 2 children) had a great time at the House on the Rocks. We appreciated the large living room sofa (great for movie night), large dining table with easy access to the kitchen (for home-cooked group meals), multiple bathrooms, very comfortable beds, and ample parking space. We were visiting for a late season snowboarding trip, and the house is conveniently located close to rental shops and Pico Mountain (and not too far to Killington resort, which we didn't visit). Our group had a comfortable and well-informed stay, and we highly recommend the House on the Rocks!

4.94 out of 5 average rating, 18 reviews

Home in Chittenden

Mountain Top Getaway Killington, Pico, VAST Trails

AlecRating, 5 stars4 months ago

We had a wonderful weekend staying at Greg and Dorie’s. The home matched the description, and was everything we needed for a few days of skiing. Greg and Dorie were super responsive and helpful. There was a big snowfall the morning of our departure and Greg helped plow us out. Snow tires are helpful! Would highly recommend this place!

4.97 out of 5 average rating, 88 reviews

Apartment in Pittsford

THE FERN: Relax in peaceful Vermont country

AndrewRating, 5 stars8 months ago

We came up for a little fall vacation to explore the local area and could not have found a better place! Absolutely beautiful location with a perfect sunset, fantastic hiking right behind the location as well. Gerd and Gisela were communicative, friendly and had really good local recommendations for spots that highlighted the trip. If I could give more stars I would

Superhost

4.81 out of 5 average rating, 54 reviews

Easy access to Rutland

MatthewRating, 5 stars2 days ago

I really like Sam's place! This was a repeat stay, and what really works for me is the location. I like to be able to park and walk to the downtown area. Sam provides lots of choices for bath amenities, and he provides all the fixin's for morning coffee/tea as well as snacks and sweet treats. The bed is very comfortable and the shower water is nice and hot. He has also installed a window unit a/c for comfort. I would highly recommend his place for your stay in the Rutland area