Family-friendly holiday rentals in Charlemont

Sunny, soaring 2-level downtown loft, scenic views

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Kitchen · Family · Cleanliness

Charming Brookside Artisan Home

Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

Kitchen · Family · Hospitality

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Kitchen · Indoor spaces · Nearby

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

Family · Indoor spaces · Biking

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Family · Kitchen · Value

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

Indoor spaces · Kitchen · Checkout

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Family · Kitchen · Value

Spacious apartment close to skiing and rafting

Located in the village of Charlemont, just one mile away from one of the region's favorite ski/mountain biking resorts, Berkshire East, is this charming apartment. Located on the second floor of the Wells Country Store, which was built in 1845 is a spacious, completely renovated, two-bedroom apartment. Come here for your country getaway and use this space as your launching pad for outdoor adventures. Hiking, fishing, white water rafting, skiing and so much more are right outside your door.

Indoor spaces · Kitchen · Accuracy

Ski, Raft & Relax | Lodge w/ Pool Table & Fire Pit

On your journey to The Lodge on Warner Hill, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located 10 minutes from Berkshire East and the Deerfield River

Kitchen · Indoor spaces · Check-in

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Indoor spaces · Family · View

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

Kitchen · Family · View

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Family · Indoor spaces · Outdoor spaces