House holiday rentals in Pittsfield

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Top-rated house rentals in Pittsfield

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Guest favourite

Home in Killington

4.91 out of 5 average rating, 167 reviews

Cozy 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 favourite

Home in Rutland

5.0 out of 5 average rating, 122 reviews

ONE ROOM SCHOOL HOUSE

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. It is now a separate, private, room. New European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace/stove for heat and atmosphere. Storage for clothing, skis, snowboards. Exterior bicycle rack. Circular driveway for off-street parking. High speed internet and 65 inch Roku TV with surround sound. Everything brand new. We have added three season screened porch.

Guest favourite

Home in Barnard

4.92 out of 5 average rating, 141 reviews

Cozy 2bd, Tennis Court, Steps to Lake, on 6 acres

This 2nd floor space is great for small groups and couples. All wood interior space has been newly updated with modern appliances, handmade slab countertops, and cozy furniture. Directly across from Silver Lake and the Barnard General Store, with 6 parklike acres including a tennis court (with pickle ball)! Easy to find, minutes from Woodstock, VT. and award-winning dining, just 3 minutes to Silver Lake State Park, and just a few miles to multiple access points of the Appalachian Trail.

Guest favourite

Home in Rochester

4.93 out of 5 average rating, 202 reviews

Porch House

Cozy house in the heart of Rochester village. Antiques and books abound, all modern amenities. Wrap around porch delightful in the summer. Walk to grocer, restaurants, pub, bakery, bookstore, art gallery, bike shop, yoga studio, farmer's market, river. Nice trails right behind house. Hiking, swimming holes, tubing, downhill/backcountry/x-country skiing, mountain/road biking, golf courses, craft breweries, distilleries, all nearby. 30 min drive to Killington/Sugarbush/Middlebury.

Guest favourite

Home in Leicester

4.98 out of 5 average rating, 137 reviews

Luxurious Cottage Massage Therapy Studio On Site

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 favourite

Home in Rochester

4.95 out of 5 average rating, 144 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 favourite

Home in Rochester

4.97 out of 5 average rating, 183 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 favourite

Home in Bethel

4.85 out of 5 average rating, 131 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.

Guest favourite

Home in Pittsfield

4.91 out of 5 average rating, 149 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

4.83 out of 5 average rating, 221 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.

Superhost

Home in Rochester

4.9 out of 5 average rating, 282 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the VT 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 lovely town of Rochester. Tubing and swimming holes nearby, tons of hiking and biking trails and berry picking nearby.

Guest favourite

Home in Rochester

4.94 out of 5 average rating, 181 reviews

The McKinley House

In the village of Rochester. Walk to bakery, cafe, tavern, grocery, and town green. Hiking, biking and Nordic ski trails! Thirty minutes to SugarBush, Pico, Middlebury, and Killington. Located in the heart of the Green Mountain National Forest. We are dog friendly but we require a conversation about it before you can show up with your dog. We charge $100 pet fee for your stay.