
Holiday houses in Chittenden
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Top-rated holiday rentals in Chittenden
Guests agree: these stays are highly rated for location, cleanliness and more.

Killington-Pico ski in/out Studio at base of Pico
At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

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.

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. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Quaint 1-bedroom cottage on Blue Ledge Farm
This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Killington VT Chalet - Lower apartment
Entire lower apt of Austrian Style home in Killington across from Pico Mtn offers beautiful views in a quiet setting with preserved forest and the Appalachian & Long Trail in our backyard. Only 2 miles to Killington Access Road. The apartment is the lower unit, owners occupy the upper unit. We are a ski family and are up early each morning. Previous reviews REQUIRED, no 3rd-party bookings. No partiers, smokers, or loud gatherings. No pets including service animals.

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

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.

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.

One Room School House. No Cleaning Fees!
Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

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.

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.

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS JUST FOR YOU PERFECT WINTER RETREAT❄️ ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes ❄️❄️SUPERHOST RATED❄️❄️ ❄️Squeaky Clean ❄️Fireplace, WIFI ❄️TV in living room & bedroom ❄️Adjustable queen bed ❄️Private covered porch ❄️Keypad check in ❄️Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.
Popular amenities for Chittenden holiday rentals
Other great holiday rentals in Chittenden

Nice, Large Modern Apartment

Charming historic Suite in Rutland City

Scenic Vermont Green Mountain Retreat

Mountain Top Getaway Killington, Pico, VAST Trails

Village House

Comfortable, relaxing large country home

Beautiful Vermont Farmhouse with stunning view

Firefly Cottage
When is the best time to visit Chittenden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $546 AUD | $625 AUD | $464 AUD | $407 AUD | $379 AUD | $346 AUD | $373 AUD | $388 AUD | $410 AUD | $335 AUD | $382 AUD | $444 AUD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
Are there pet-friendly house rentals in Chittenden?
Four-legged friends are welcome in Chittenden. Choose from more than 20 house rentals for guests traveling with pets.
Do apartment rentals in Chittenden have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Chittenden. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chittenden?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with free parking, over 50 homes with a kitchen, over 50 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Chittenden vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chittenden, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Chittenden have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chittenden have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chittenden?
Chittenden has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Chittenden?
Experience the best of Chittenden with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chittenden have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Chittenden?
Yes! Work meets play with ease at over 40 house rentals in Chittenden featuring dedicated workspaces. Stay connected and productive in your home away from home.
Quick stats about holiday rentals in Chittenden

Total holiday rentals
Explore 100 holiday rentals in Chittenden

Nightly prices starting at
Chittenden holiday rentals start at $134 AUD per night before taxes and fees

Verified guest reviews
Over 4,500 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
100 of Chittenden holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chittenden rentals

4.9 Average rating
Chittenden stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fireplace Chittenden
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- Pet-friendly rentals Chittenden
- Family-friendly rentals Chittenden
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- House rentals Chittenden
- Rentals with a patio Chittenden
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- Rentals with a fire pit Chittenden
- Okemo Mountain Resort
- Stratton Mountain
- Lake George
- Sugarbush Resort
- Killington Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Bolton Valley Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Cochran's Ski Area
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Montshire Museum of Science
- Adirondack Extreme Adventure Course
- Middlebury College
- Shelburne Vineyard
- Trout Lake
- Camp Plymouth State Park
- Southern Vermont Arts Center




