Holiday rentals in Monson

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

The Silo | Architectural Retreat Near UMass

A unique circular Silo stay five minutes from UMass & Amherst College, directly abutting the 20-acre UMass Stockbridge School of Agriculture Farm. Curved walls, warm wood, and changing natural light- designed for connecting to the landscape. Guests have a fully private entrance and private interior space. Best suited for ages 13+; no animals due to severe allergies. Sleeps 4: queen loft bed + sofa converts to bed + air mattress; 1 bathroom- ideal for couples or close friends.

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

The Hampden House

Escape to serenity at our small home nestled in peaceful Hampden, outside Springfield. With its open and roomy layout, this charming property provides ample space for families to relax and unwind together. The fully fenced yard is perfect for kids and pets to run and play safely. If you're seeking a relaxing retreat or just passing through, our home has something for everyone. Book your stay and experience the serenity of country living, perfect for creating family memories.

Charming water front cabin with boat dock

Escape to our charming lakefront cabin! This cozy retreat offers a peaceful getaway with direct access to the sparkling waters and a private dock for swimming, fishing, and kayaking. Unwind on the inviting covered porch sipping your morning coffee while mesmerizing a spectacle sunrise or gather for a barbecue while relishing the panoramic lake views. Whether you're seeking a romantic weekend or an outdoor adventure, this lakeside haven promises an unforgettable experiences!

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

3 BR with Private Balcony & Deck

*Spacious Layout: Features 3 separate bedrooms and a cozy loft area for extra sleeping space. *Stylish Accommodation: Perfect for group and family trips or a romantic getaway. *Central Location: Situated in Downtown Stafford with a beautiful view overlooking Middle River. *Well-Equipped: Includes a washer/dryer, a chef’s kitchen and all necessary amenities. *Yoga Studio Access: Home to Middle River Yoga Studio, located just across the hall.

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.

The Carriage House

Private 1BR carriage house apartment in Tolland, CT, 5 min to I-84 and 15 min to UConn. Separate entrance with no shared spaces. Includes full kitchen, Wi-Fi, laundry, parking, and Level 2 EV charging. Sleeps up to 4 with optional queen mattress. Quiet wooded setting. Self check-in. No pets, smoking, or parties. Some light noise possible from upstairs unit.