Tiny house holiday rentals in Cheshire County

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

~Luxury Tiny Cabin~

Enjoy an intimate weekend escape in our 400 sq ft Tiny Cabin, located in Southern Vermont! This Home overlooks gorgeous hardwoods and seasonal foliage. Listen to the sound of the brook bustling by while nestled on the spacious front porch, sipping a hot cup of coffee or cocoa! 'Tis the season for glamping and our luxury tiny home experience is just what the doctor ordered! Make sure to cross this off your bucket list; about 45 minutes from Mts Okemo and Killington, 5 minutes from local stores!

Charming Waterfront Log Cabin

Escape the daily grind at this unique & tranquil getaway. At the end of a quiet road, this vintage log cabin sits on a 150-acre pond with access to kayaks to explore at your pleasure. Inside, the space features 2 bedrooms & a spacious loft. Listen to the sounds of nature by the fire pit, watch the sunset from the porch, paddle on the pond, or watch Netflix on our fiberoptic Wi-Fi. However you slice it, you'll leave The Pond Camp relaxed, rejuvenated, & ready to tackle whatever comes your way.

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Cozy Cabin in the forest

This cabin is a peaceful sanctuary ideal for meditation or self-reflection. Situated in a beautiful woodland setting, visitors can connect with nature and participate in various wellness activities. Yoga sessions, sauna and cold plunge (upon request), and parking are available on the property. Surrounded by 200 acres of conservation land for walking, hiking, cross country skiing and snowshoeing. Amenities include a wood stove for heat, an outhouse toilet, and Coleman stove for cooking.

Settlers Cottage on Spofford Lake

This perfect spot on Spofford Lake will have you coming back every year to make memories without giving up the comfort of home. Plenty of space for everyone inside and out. Comfortably sleeps 4 people. There's so much to enjoy: from a cup of coffee sitting on the beach, to swimming, kayaking, paddle-boating, enjoying sunsets while making s-mores for the kids at the campfire, grilling burgers with family and friends, and even streaming your favorite shows on a rainy day.

Detox Healing Sanctuary with Wood-Fired Sauna

Escape the city & take a break from hectic schedules & life's demands. We invite you to embrace life at a relaxed pace surrounded by nature on our 1810 farm. Enjoy the fire pit, walk the trails, forage for treasures & unwind in the wood fired sauna! Rest and reset your life & cultivate space for stillness & healing We've created a place for you to unwind & restore your soul, & detox & recharge your body. For the full retreat ask about day pass to Covey House Spa

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Off the grid in Surry NH

PLEASE READ BEFORE BOOKING If you like to camp but prefer a bed, this cabin is for you! You supply all of your own camping equipment and we will provide four walls and a futon in this TINY (8x8) cabin. There is no electricity or running water, we do supply a couple of solar lights, a fire pit and wood, small card table and 2 foldable chairs and a cooler (you bring the ice). An outhouse is a few steps away. We do not allow dogs.