
Places to stay near Mount Sugarloaf State Reservation
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Mount Sugarloaf State Reservation
Guests agree: these stays are highly rated for location, cleanliness and more.

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

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.

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.

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!

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.

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!

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).

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!

Perfectly Polished Deerfield Home 5 min to I-91
A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

A Country Retreat-Enhanced Studio Apartment
Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Forest Hideaway—Light, Privacy, Washer/Dryer
Wake up among 100-year-old trees, then drive ten minutes into Amherst for museums or sushi. Or hike out the door toward wooded trails. The apartment sits with our house on 5 acres of mature forest. With a kitchen & washer/dryer, the apartment is peaceful and practical, ideal for a weekend getaway or an extended stay, great for academics needing space for contemplation or for a couple visiting family. (Read about the steep driveway if planning a winter trip.)

Cozy get-away!
This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing, TV-free space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!
Popular amenities for holiday rentals near Mount Sugarloaf State Reservation
Other top sights near Mount Sugarloaf State Reservation
Apartment rentals with wifi

Mount Snow Ski Chalet

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Mt Snow Ski In/Out at Seasons

Winter Dream! The Handle Lodge at Snowtree Condos

Seasons Condo on mtn-sports center-pool-Ski in-out

3 Bedroom, 2 Bathroom Condo, 2 Mins to Mount Snow!

Walk to Mt. Snow-Spa-Summer Pool

Mount Snow Close, Great Price, Lots of Room
Family-friendly house rentals

Farm Fresh Feeding Hills

Charming and Cozy Hilltop Home

Vermont Botanical Studio Apartment

Sunderland house - 5 College area

Stone n' Sky Lodge

Cozy Vermont mini-house

Modern Comfort Meets Northampton’s Vibrant Charm

Little House Inn - Private House - Secluded
Apartment rentals with air conditioning

Soaring 2-level loft w/ views in heart of downtown

Farm land view.

Annies’ Place by The Bridge of Flowers ~

Steps to MoCA Near SKI: 2bd + SAUNA!

The cozy clubhouse

Cozy Haven: Convenience & Charm

Sweet Retreat minutes from Northampton & Amherst

Ensign House Room
Other great holiday rentals near Mount Sugarloaf State Reservation

Tiny House Farm Retreat: Mountain Views, Fire pit

Peaceful Cabin in the Woods

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

hope house

Rustically Romantic Cabin Near Sweet Pond

Windy Top Cottage ~ A Romantic "European" Getaway

Under the Hemlocks Escape: A Cozy Getaway Retreat

Treehouse Haven in Putney-All Seasons
Destinations to explore
- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Mount Greylock Ski Club
- Bushnell Park
- Brimfield State Forest
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Bright Nights at Forest Park
- Wintonbury Hills Golf Course
- Bigelow Hollow State Park
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Bousquet Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Talcott Mountain State Park
- Beartown State Forest
- Hartford Golf Club
- Mount Tom State Reservation
- Berkshire Botanical Garden
- Hooper Golf Course
- Pineridge Cross Country Ski Area




