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.

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Top guest favorite
An open-concept living area showcases rustic wooden beams and large windows, allowing natural light to fill the space. A dining table with wooden chairs is positioned near the kitchen, which features modern appliances and a cozy wood stove on a stone base.
Home in Granville

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
Top guest favorite
Home in Woodstock

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
Superhost
Home in Killington

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
Guest favorite
A spa-like bathroom features a luxurious soaking tub beside a modern shower enclosed by glass. Multiple windows offer views of the wooded surroundings, while elegant wood accents complement the radiant floor heating. A stylish sink and cabinetry enhance the tranquility of the space.
Home in Pittsfield

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
Guest favorite
A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.
Home in Stockbridge

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
Guest favorite
An aerial view showcases the expansive 10-acre estate surrounded by snow-covered mountains. The property features a serene, spring-fed pond reflecting the landscape, with a spacious home nestled near the water, offering an inviting retreat in a tranquil setting.
Home in Pittsfield

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
Top guest favorite
A spacious living area features a large leather sectional sofa facing a glass coffee table. Natural light floods in through multiple large windows, framed by dark trim. A cozy reading nook is seen in the corner, adorned with a decorative throw and a small side table.
Home in Pittsfield

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
Guest favorite
Home in Pittsfield

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
Guest favorite
Home in Pittsfield

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
Top guest favorite
Home in Pittsfield

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
Top guest favorite
A cozy bedroom features a spacious king bed dressed in a plaid blanket, complemented by decorative pillows. Two bedside lamps provide soft illumination. A wood shelf above the bed holds decorative items. A large window offers a view of the outdoors, dressed with light curtains.
Home in Killington

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
Top guest favorite
A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.
Home in Rochester

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 reviews

Popular amenities for Pittsfield house rentals

When is the best time to visit Pittsfield?

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Avg. priceG$102,108 GYDG$108,595 GYDG$78,255 GYDG$76,372 GYDG$76,372 GYDG$76,372 GYDG$68,003 GYDG$64,445 GYDG$68,003 GYDG$74,280 GYDG$77,000 GYDG$94,157 GYD
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