Family-friendly holiday rentals in Pittsfield

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Breadloaf Hut. Glamping, hiking, biking, foliage

Hiker, writers’, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire.

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Tiny House on Vermont Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Disconnect to reconnect. Our homestead is based on permaculture landscape design.Relax by the living pool, unwind in the traditional sauna, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay and Upper Yurt on VT Homestead

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Suite in the Green Mountains

We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

Apple Hill Cabin at Four Springs Farm

Privately located walk-in camping sites are part of this beautiful working organic farm on a west-facing Vermont hillside. Guests will be dazzled by star-studded skies, treated to spectacular sunsets, and entertained by the two young farm cats. The farm is mosquito free but has millions of fireflies in summer. Have fun exploring. It's nature's playground at her best!!!