Holiday rentals in Monson

Victorian Retreat in quaint New England Town

Welcome to your home away from home in the heart of Palmer, Ma! This beautifully remodeled 175-year-old Victorian offers the perfect balance of historic charm and modern comfort. Enjoy spacious living areas, updated kitchen and baths, and tasteful furnishings that make your stay both comfortable and convenient. You’ll have off-street parking, a private entrance, and a relaxing small-town atmosphere — ideal after a long shift or day of meetings. Perfectly situated for traveling professionals!

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.

Brimfield Bungalow 31 near flea market &Sturbridge

Escape to this Updated bungalow near Sturbridge, perfectly nestled in the peaceful town of Brimfield. Just a short drive from downtown, our beautifully decorated home offers a serene retreat with access to Sherman Lake. Featuring 2 comfortable bedrooms, this cozy retreat is close to Sturbridge for easy access to restaurant row as well as the many breweries and wineries in the area. Enjoy the many walking trails and/ or the one and only Brimfield Antique Show/Flea Market just minutes away.

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

Warm 3 BR house w/ fenced yard close to everything

Charming and historic 3-bedroom home with a fenced backyard and off-street parking, accommodating up to 8 guests. Nestled in a quiet neighborhood, featuring an updated kitchen, formal dining room, and cozy living room. Conveniently located just a short drive from the Naismith Memorial Basketball Hall of Fame, MGM Casino, Dr. Seuss Museum, Titanic Museum, Springfield Armory, MassMutual Center, Six Flags, The Big E, and several colleges/hospitals. This is an entire house—no shared spaces.

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 Silo | Architectural Retreat Near UMass

A unique circular Silo stay five minutes from UMass & Amherst College, directly abutting the 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.

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.

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.

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

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 studio loft

Cozy studio apartment in a quiet, wooded setting in Tolland, CT—just minutes from I-84 and 15 minutes to UConn. Sleeps 2–4 with a queen bed and optional mattress. Includes full kitchen, bathroom, fast Wi-Fi, private entrance, and easy self check-in. Free Level 2 EV charging and plenty of parking. Ideal for short or extended stays. No pets, no smoking, no parties.