Vacation rentals in Dragon Hill

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Top-rated vacation rentals in Dragon Hill

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Top guest favorite

Home in Shelburne Falls

5 out of 5 average rating, 105 reviews

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.

Guest favorite

Apartment in Conway

4.98 out of 5 average rating, 106 reviews

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the local ski resort Berkshire East. There are many sights, country roads, trails to explore, along with many varied excellent restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Top guest favorite

Guesthouse in Shelburne Falls

5 out of 5 average rating, 283 reviews

Shelburne Guest House -The Ranch

The nice thing about my home in Shelburne is the location & the peace & quiet. 10 minute drive to Greenfield Rotary I-91, easy drive to Amherst, Smith, UMass, NMH, Deerfield Academy & Stoneleigh Burnham School. Berkshire East nearby for outdoor sports. 5 minute drive to the Village of Shelburne Falls, hiking trails, bike paths, High Ledges, & the Bridge of Flowers. Updated 1964 Sears Roebuck catalog home. Bright & sunny! Large farmhouse kitchen, 3 cozy bedrooms. Large yard! Your Vacation Home!

Top guest favorite

Guest suite in Greenfield

4.95 out of 5 average rating, 209 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Top guest favorite

Apartment in Shelburne Falls

4.96 out of 5 average rating, 366 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

Top guest favorite

Guesthouse in Cummington

5 out of 5 average rating, 133 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Superhost

Guest suite in Montague

4.91 out of 5 average rating, 226 reviews

Great Falls Private Suite

Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the Connecticut River. Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon, 2 miles from downtown Turners Falls and 2.6 miles from downtown Greenfield. If you are looking for a private and bright suite with beautiful natural light and a modern bohemian feel this guest retreat is for you. I look forward to hosting you!

Top guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 307 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favorite

Apartment in Shelburne Falls

4.89 out of 5 average rating, 175 reviews

Mountain+river views from big, sunny downtown flat

Walk to everything from this sunny, spacious, tastefully furnished apartment, newly renovated in 2023, in the heart of downtown Shelburne Falls steps from Bridge of Flowers. Giant windows in all directions with views of town, mountains & river. Queen bedroom & comfy pull-out queen bed in the living room. Large, well-equipped eat-in kitchen with brand-new stainless-steel appliances & dishwasher. Washer/dryer. Luxurious bathtub & rain shower. plenty of closet space. Fast Internet. 65" Roku TV.

Top guest favorite

Camper/RV in Guilford

4.94 out of 5 average rating, 170 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

Guest favorite

Apartment in Shelburne Falls

4.97 out of 5 average rating, 589 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Top guest favorite

Cabin in Guilford

4.99 out of 5 average rating, 149 reviews

Rustically Romantic Cabin Near Sweet Pond

COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES