
Holiday rentals with a fireplace in Pittsfield
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Top-rated rentals with a fireplace in Pittsfield
Guests agree: these rentals with a fireplace 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.

Elegant Alpine Condo
Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Killington Reg #007718

Hancock hideaway
Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

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.

Ski Back to Trail Creek!
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!

A million-dollar view near Killington on 60 acres.
This secluded 200 + year old mountain farmhouse is located in the small town of Pittsfield, VT just 5 minutes away from one of the most scenic drives in New England, Route 100. Surrounded by national forest with stunning views of the Green Mountains, this is the perfect place to get away with family or even by yourself. Plenty of room outside on the 60+ acre property with fields and a small pond. In the center of Vermont, it's the perfect home base.

Gnome Home Mountain Ski Chalet w/Sauna Killington
Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

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.

Beautiful Spacious Condo at Killington Resort
This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Cozy Condo- Close to Mountain, Ski home trail
Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!
Popular amenities for rentals with a fireplace in Pittsfield
House rentals with a fireplace

BEST Views! Close to Silver Lake + Woodstock VT

Private Oasis Under 10 Mins from Woodstock

Escape to Vermont

Epic Views of the Green Mountains

The Barnbrook House

Affordable, private, 30 min to Killington

Secluded Log Cabin with Unrivaled Views!

Modern Farmhouse on 25 Acres - Superb Views
Apartment rentals with a fireplace

The Barn at Middlebury

Peaceful Ludlow Base 5 minutes to Okemo

Spacious Home Near Heart of Middlebury Fiber Wifi

Dog Team Falls Apartment - Minutes from Middlebury

Canyons Unit: Skyeship Gondola 2 miles w/HOT TUB

Doc's Lake House 1st floor, 2 bdrm full apartment

Spacious One Bedroom - Walk To Town, Restaurants

Bluebird Studio- Light filled and airy
Villa rentals with a fireplace

Cozy, Comfy & Sunny Renovated Sugarbush Condo

Private Wing of largest Colonial Mansion in US

Pico D305 located slope side at Pico quiet area

Sunrise East Glade C8 Ski on Ski off

Sunrise Timberline I7 Ski on Ski off

Whiffletree base of Killington outdoor pool

Base of Killington with Sports center access

Base of Killington with Sports center access
When is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 368 | € 370 | € 320 | € 277 | € 274 | € 255 | € 274 | € 259 | € 259 | € 274 | € 313 | € 371 |
| 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 holiday rentals with a fireplace in Pittsfield

Total holiday rentals
Explore 50 holiday rentals in Pittsfield

Nightly prices starting at
Pittsfield holiday rentals start at € 160 per night before taxes and fees

Verified guest reviews
Over 2,000 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Pittsfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pittsfield rentals

4.9 Average rating
Pittsfield stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a hot tub Pittsfield
- Rentals with a fireplace Rutland County
- Rentals with a fireplace Vermont
- Rentals with a fireplace United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Montshire Museum of Science
- Adirondack Extreme Adventure Course
- Mount Sunapee Resort
- Dartmouth College
- Middlebury College
- Shelburne Museum
- Trout Lake
- Southern Vermont Arts Center
- Shelburne Vineyard
- Warren Falls
- Emerald Lake State Park




