
House vacation rentals in Pittsfield
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Quick stats about house rentals in Pittsfield

Total vacation rentals
Explore 50 vacation rentals in Pittsfield

Nightly prices starting at
Pittsfield vacation rentals start at G$29,293 GYD per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Pittsfield vacation rentals include wi-fi 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!
Top-rated house rentals in Pittsfield
Guests agree: these houses are highly rated for location, cleanliness, and more.

Epic Views of the Green Mountains
Luxurious bohemian style overlooking one of the most epic views in the Green Mountains. Surrounded by 25,000 acres of National Forest and complete seclusion, yet just a short ride from several towns. Spacious, immaculate, modern home with rustic beams and gorgeous wood floors. Each of the three bedrooms (and baths!) have a wonderful view. The master bedroom is massive and has sweeping views out over the Battell Wilderness and the Long Trail. The front of the cottage is a wall of windows overlooking a beautiful pond and the Green Mountain National Forest. No light pollution. No noise except for the tree frogs and the sound of the White River rushing over the rocks far below in the hollow. It's worth mentioning that Breadloaf Mountain Cottage was a gift that I am grateful for. I still can't believe that I am so lucky to be able to enjoy it frequently. Please understand that those sweeping, epic views you see all around you when you are there, come at a price. Being perched atop a mountain in the wilderness has obvious benefits, but due to frequently changing weather, access and utilties are sometimes a bit more tricky than something in town. Please be prepared to be patient with the weather and the WIFI. While my internet is as good as anywhere in Vermont, it is a rural network and is likely more quirky than urban or suburban utilities. I have a 20mbps service. Breadloaf Mountain Cottage is at the top of a ridge that runs parallel to scenic Route 100. It sits at about 1600 feet above sea level. While completely secluded, it is just 1.3 mile to the Granville Store, and just a few minutes more to Hancock, Rochester and Warren. You could spend weeks just exploring the hiking, biking, swimming and fishing opportunities right from the property! Breadloaf Mountain Cottage is located on Forest Road 55, just off scenic Route 100. While it is easily accessible year round, a 4X4 or AWD vehicle is highly recommended in snow and mud. Quality AT or snow rated tires are a must in the winter. This is true generally in Vermont. Come prepared.
ValueFamilyParking
4.96 out of 5 average rating, 177 reviews
Cape Cod Home in Woodstock, Pet-Friendly & Wooded
Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to
ValueLocationKitchen
4.99 out of 5 average rating, 170 reviews
Luxury Condo Tucked in the Heart of Killington
Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!
ValueFamilyBackyard
4.86 out of 5 average rating, 260 reviews
Romantic Retreat, Hot Tub, near Killington Mtn
This architect-designed, contemporary mountain chalet features all the classic elements – including stone fireplace with wood stove, soaring vaulted wood ceilings, walls of glass and wide pine floors. This stunning home has a lovely wooded backdrop adjacent to Hawk Mountain pond. It is located in Pittsfield, 8 miles from Killington. Kitchen has high-end appliances, quartz countertops and custom backsplash. Stunning spa-like oasis bathroom. Several decks, fire pits, next to pond.
LocationFamilyLayout
4.93 out of 5 average rating, 56 reviews
Escape to Vermont
Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.
ValueLocationHiking
4.88 out of 5 average rating, 161 reviews
Mountain Top - Fresh Pond - Killington - Hot Tub
This magnificent 10-acre estate - ~15 minutes away from Killington and Pico resort - offers breathtaking views of the Killington and Pico ski slopes and the lush Green Mountains, creating an invigorating and awe-inspiring setting. The property's oasis-like atmosphere features a 12-foot-deep spring-fed pond and a stream that provides abundant fresh water, perfect for taking a dip and enjoying the outdoor shower. Please note that the indoor fireplace has been disabled for safety reasons
FamilyLocationSleep quality
4.95 out of 5 average rating, 41 reviews
Skyeburst | Modern Mtn Home
| Welcome to The Skyeburst House | Reimagined 1970's Mountain Home 15 mins from the Killington K1 Gondola. This is a newly renovated modern home boasting lots of natural light, spa like bathrooms, open floor plan, and exposed cathedral ceilings. Curated with a mix of rustic and modern decor. High quality king and queen beds. Modern appliances. Samsung 75" QLED 4K TV. Sonos Sound System. Fire pit. Deck. Grill. Stars. Your Vermont adventure awaits.
LocationFamilyTV
4.98 out of 5 average rating, 46 reviews
Mountain Home with Scenic Views
A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from Killington and Pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.
LocationFamilyIndoor spaces
4.81 out of 5 average rating, 16 reviews
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.
LocationFamilyNearby
4.85 out of 5 average rating, 256 reviews
NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals
BRAND NEW HOME. You want the mountain access without the condo noise. Powder Run is your answer. It is a brand new 2,100 sq. ft. sanctuary on the Pittsfield border of Killington. Park in the flat driveway, plug in your EV, and dry your boots in the mudroom. Whether you are soaking in the private hot tub or gathering by the red enamel gas stove, this is where the adventure slows down. Sleeps 8 with AC and generator.
LocationFamilySkiing
5.0 out of 5 average rating, 20 reviews
CozyDen - AC, Bike to Mountain, Porch!
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!
FamilyValueLaundry
4.98 out of 5 average rating, 218 reviews
Modern Farmhouse on 25 Acres - Superb Views
This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.
ValueLocationView
4.97 out of 5 average rating, 157 reviewsPopular amenities for Pittsfield house rentals
House rentals with a pool

Ranch at Mendon Mt Orchards
ValueFamilyBreakfast
4.87 out of 5 average rating, 283 reviews
Golf and Mountain Biking outside the door!
FamilyLocationGetting around
4.89 out of 5 average rating, 141 reviews
Luxury Mid-Century Modern Vermont Home, Okemo View
FamilyValueWifi
4.99 out of 5 average rating, 101 reviews
Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
FamilyLocationNearby
4.92 out of 5 average rating, 172 reviews
Historic Farm Stay | Heated Pool + Hot Tub
FamilyLocationSleep quality
4.98 out of 5 average rating, 214 reviews
Ski Mountain View Estate
ValueFamilyWifi
4.96 out of 5 average rating, 142 reviews
Classic VT Ski Chalet - Walkable to Okemo Ski Lift
LocationFamilyCondition
4.92 out of 5 average rating, 114 reviews
Beautiful Bromley/Manchester VT Retreat w/hot tub
FamilyLocationComfort
4.9 out of 5 average rating, 184 reviewsWeekly house rentals

Green Mountain/Killington Getaway
ValueFamilyWalkability
4.84 out of 5 average rating, 88 reviews
VT Cabin, close to Killington Mountain and lakes.
ValueFamilyKitchen
4.96 out of 5 average rating, 49 reviews
Skye Ridge Lodge: Private Hot Tub, Open Concept
LocationFamilyHospitality
4.96 out of 5 average rating, 45 reviews
Killington Chalet: Hot Tub, Fireplace, spacious 4b
FamilyLocationCheckout
4.95 out of 5 average rating, 81 reviews
The Merak Haus – a wooded retreat
LocationFamilyNearby
5.0 out of 5 average rating, 9 reviews
Hot Tub|Sauna|Relax! 5 mins to downtown Killington
ValueFamilyCleanliness
4.98 out of 5 average rating, 56 reviews
Cedar Wood Lodge
FamilyLocationAmenities
5.0 out of 5 average rating, 17 reviews
Ski Home/Arcade Mountain Views Near Killington/Woo
LocationFamilyHospitality
5.0 out of 5 average rating, 22 reviewsPrivate house rentals

Rockwell Haus: modern cabin 14 min from Killington
FamilyLocationCheck-in
5.0 out of 5 average rating, 23 reviews
Killington Ski House
LocationFamilyBathroom
4.9 out of 5 average rating, 52 reviews
Killington family friendly all season house
FamilyValueTV
4.86 out of 5 average rating, 100 reviews
Riverfront Retreat in Stockbridge
LocationFamilyParking
5.0 out of 5 average rating, 42 reviews
Chalet Suite | 2BR+Loft (15 min to Killington Mtn)
LocationFamilyAccess
4.97 out of 5 average rating, 30 reviews
2 Min Walk to Woodstock Village Mountain Views
FamilyLocationHiking
5.0 out of 5 average rating, 30 reviews
1800s Farmhouse with River Access. Private w/ Land
LocationFamilyHiking
4.95 out of 5 average rating, 38 reviews
The Fiddlehead Lodge (Green Mountain Getaway)
LocationFamilyAccess
5.0 out of 5 average rating, 14 reviewsWhen is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$102,108 GYD | G$108,595 GYD | G$78,255 GYD | G$76,372 GYD | G$76,372 GYD | G$76,372 GYD | G$68,003 GYD | G$64,445 GYD | G$68,003 GYD | G$74,280 GYD | G$77,000 GYD | G$94,157 GYD |
| 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 |
Destinations to explore
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Dartmouth College
- Fort Ticonderoga
- Middlebury College
- Hildene, The Lincoln Family Home
- Killington Resort
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Montshire Museum of Science
- Trout Lake
- Warren Falls
- Camp Plymouth State Park
- Shelburne Vineyard
- Shelburne Museum
- Cold Hollow Cider Mill
- Quechee Gorge





