
House holiday rentals in Chittenden
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Top-rated house rentals in Chittenden
Guests agree: These houses are highly rated for location, cleanliness and more.

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!
Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mnt views, peaceful brook on 1+ acre. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV/nintendo switch.

Home Sweet Home
Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Cozy Contemporary Downtown Texaco
Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Bill’s Barn Rochester Vermont 3 Bdrm entire house
Our place is a 1980's barn/woodshop that never housed animals that has been converted into a lovely three bedroom home.We are 20 minutes from Rikert 2019 hosts of the Bill Koch Festival and the Middlebury College Snow Bowl.The place is light and airy with southern and eastern sun.The main living room has 13 foot ceilings with lots of couches, arm chairs and places to hang out, read and or relax.We are in the heart of the Green Mountains with skiing and colleges, an easy drive from the house.

COZY home, great location, W/D, & Full Kitchen!
Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

Cozy Home in Poultney, Vermont.
If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

Upstairs Adventurer's Retreat
Welcome to this peaceful and centrally-located space in historic Pittsford. Situated near the top ski and mountain bike attractions in central Vermont, incredible trails, Middlebury, Rutland, Killington, Pico, Mountain Top Resort, and 45 minutes east of Woodstock, this couldn't be in a better location. This property has been in existence since 1832, and lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. Small but comfortable.

The Guest House at Sky Hollow
This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Bear Creek Lodge
This ski chalet just off the Killington Access Road features exposed-beam vaulted ceilings and a front porch. Enjoy the peaceful running creek along the back of the property. Inside, you'll have a cozy mountain atmosphere plus an extensive collection of board games and DVDs for those rainy days or for warming up after a day in the snow. Full kitchen for group meals and plenty of parking. Close to the slopes, restaurants, and all the area attractions!

Trail Creek - ski home!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

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.

Killington area home - 4 seasons - hot tub and A/C
Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.
Popular amenities for Chittenden house rentals
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

Ranch at Mendon Mt Orchards

Topridge Ski-on/Ski-off | 4BR w Game Room!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dana Road House Sunlit VT Country Home w/HotTub

Comfortable, relaxing large country home

Luxurious family retreat home in the mountains
Weekly house rentals

Charming Vermont Schoolhouse

Skyeburst | Modern Mtn Home

Mountain Getaway Pet friendly

Entire home- Killington, Vermont Ski, Hike, Bike

The Looking Glass, a modernistic escape

Cozy Cape-Style home near Killington, VT

Cozy Killington home - Private Hot Tub

Bear Paw: 3 Living Zones, Hot Tub, 5 Mins to Pico
Private house rentals

Chalet Suite | 2BR+Loft (15 min to Killington Mtn)

Modern Killington A-Frame with Deck & Hot Tub

Fun In Fun Out Up: 3BR, 2BA. Hot Tub. Sauna.

Fred Eddy Farmhouse

Killington Mountain Farmhouse-5 min to Skiing

Mountain Top Getaway Killington, Pico, VAST Trails

Village House

Romantic Retreat, Hot Tub, near Killington Mtn
When is the best time to visit Chittenden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $667 AUD | $706 AUD | $572 AUD | $555 AUD | $519 AUD | $485 AUD | $485 AUD | $477 AUD | $457 AUD | $479 AUD | $463 AUD | $610 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 |
Quick stats about house rentals in Chittenden

Total holiday rentals
Explore 60 holiday rentals in Chittenden

Nightly prices starting at
Chittenden holiday rentals start at $309 AUD per night before taxes and fees

Verified guest reviews
Over 1,720 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi 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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- Pet-friendly rentals Chittenden
- Rentals with a hot tub Chittenden
- Rentals with pools Chittenden
- Rentals with a fireplace Chittenden
- Rentals with a fire pit Chittenden
- Rentals with a patio Chittenden
- Family-friendly rentals Chittenden
- Rentals with a washing machine and dryer Chittenden
- Rentals with outdoor seating Chittenden
- House rentals Rutland County
- House rentals Vermont
- House rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Montshire Museum of Science
- Dartmouth College
- Adirondack Extreme Adventure Course
- Shelburne Museum
- Middlebury College
- Southern Vermont Arts Center
- Emerald Lake State Park
- Shelburne Vineyard
- Trout Lake




