House vacation rentals in Pittsfield

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Top-rated house rentals in Pittsfield

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Guest favorite

Home in Killington

4.9 out of 5 average rating, 184 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!

Guest favorite

Home in Barnard

4.98 out of 5 average rating, 124 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Guest favorite

Home in Killington

5 out of 5 average rating, 102 reviews

The Big Lebearski! Hot Tub, FirePit

The Big Lebearski is a modern Killington home located just off the main road and close to everything. While you relax at our home after a day on the mountain, you can catch a movie on one of our smart TVs, relax in the outdoor hot tub, roast s'mores at the fire pit, enjoy a drink at the motorcycle bar, shoot hoops in the game room or sit by the wood burning fire. This home is perfect for groups and families to spread out and enjoy all that Killington has to offer. Central AC - rare in Vermont!

Superhost

Home in Rochester

4.9 out of 5 average rating, 288 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with large deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town of Rochester. 35 min. to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. *Snow tires or chains needed from Dec-March. When you book, please tell us that you saw the recommendation.*

Superhost

Home in Stockbridge

4.87 out of 5 average rating, 141 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.

Guest favorite

Home in Leicester

4.97 out of 5 average rating, 162 reviews

Pristine Cottage, Grand Piano, Massage Studio

Meticulously clean, private getaway, custom built home to yourself. Beam ceilings, wood floors, oriental carpets, Alexa, grand piano & lots of art. Complete kitchen, pancake mix & Vt maple syrup. Coffee, teas, orange juice, bagels, cream cheese, granola & fruit. Shower bath with shampoo, conditioners, body wash etc. New private deck, tables & chairs... outside art work. Massage available in log cabin on site $70 Ninja Warrior outside gym with trampoline & slack line

Guest favorite

Home in Rochester

4.95 out of 5 average rating, 153 reviews

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 196 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road 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!

Guest favorite

Home in Bethel

4.85 out of 5 average rating, 145 reviews

Hike, run, swim or cycle in beautiful Central VT

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Superhost

Home in Killington

4.84 out of 5 average rating, 101 reviews

Bear Creek Lodge

This ski chalet just off the Killington Access Road features exposed-beam vaulted ceilings and a wrap-around 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!

Guest favorite

Home in Pittsfield

4.91 out of 5 average rating, 158 reviews

Beautiful Mountain Log Cabin 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.

Superhost

Home in Pittsfield

4.84 out of 5 average rating, 226 reviews

Killington area home - 4-seasons & hot tub

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, 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.