Waterfront holiday rentals in Western Massachusetts

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

Rustic Pond Cabin: Nature, Stars & Serenity

Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

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!

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

The Red Cabin-Secluded Getaway with backyard Brook

Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Chic Downtown Studio, Perfect for College Weekends

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

King Bed, Wi-Fi, 2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Smart TV

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Waterfront 1-bedroom apartment on 5 acres

This space has its own entrance/key and is attached but separate from the main house. Apartment has outstanding Western waterfront views and sunsets. Space is appropriate for 1-3 people and there is parking for 1 car. Guests have their own private apartment but shared outside amenities including patio, firepit, playset, yard, grill, kayaks, paddleboards, canoe, and dock seasonally May-September. Shared outdoor 7-person hot tub.

Hill-Ross Guest Suite

You'll have the Guest Suite at The Historic Hill-Ross Homestead with private entrance all to yourself. Guest Suite is the renovated carriage house ell off the main farmhouse which houses 2 bedrooms, 1 kitchen, 1 living room and 1 bathroom including your own private patio. One bedroom has a queen bed and second bedroom has a full bed and a single bunk bed. Hill Ross Homestead is a short, 5 minute walk into downtown Florence.