Family-friendly holiday rentals in Northampton

Cheery artist's studio in Florence

This 2nd floor guest suite in my home has a private entrance via an outdoor set of stairs (See Guest access section for details), full kitchen, and bathroom (tub but no shower). The open floor plan includes a front room with twin bed and a smaller TV room with futon sofa that I convert to a double bed as needed. Originally my art studio, I now offer it for short-term stays. COVID-19 policy. I allow 24 hours between bookings (no same-day turnovers). I request that my guests be fully vaccinated.

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Light-bathed comfort, wood + charm, right downtown

Two blocks from Main St & steps from Smith College, in the heart of vibrant downtown, this sun-flooded 2br apt/terrace with original 1890s wood floors is in the home of the family behind Northampton's iconic Inspirit Crystals shop. Your 2 south-facing BRs (1 w/sitting area) are drenched in sunlight. A fully equipped eat-in kitchen opens onto a small private terrace with café seating for 2 overlooking tree-shaded Trumbull Rd. Shared outdoor pool, garden w swing, play gym & sandbox for kids' use.

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Gorgeous Getaway

Brand new construction and state-of-the-art styling make this first-floor apartment a one-of-a-kind masterpiece. Every detail has been meticulously planned to ensure your visit is memorable! Just minutes from downtown Northampton, this stunning apartment features a spacious king-size bedroom with a private bath that includes a beautifully tiled walk-in shower, a second queen-size bedroom, a gorgeous kitchen with quartz countertops, and a beautiful living room with a flameless fireplace.

Private Guest House Downtown Noho

A one bedroom cozy guest house with a private entrance located on Market St. in downtown Northampton. Cozy and comfortable queen size bed with super soft bedding, full bathroom, and lots of privacy. Quirky space tucked behind Jo Smith's Art Gallery- quiet brick building with an 'inner room' for guests. You pass through the outer room, which is more storage space than living space and the inner space is a one room bedroom/bathroom with no kitchen. This space is not set up for cooking.

Modern Comfort Meets Northampton’s Vibrant Charm

Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

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.

Large Quirky Sunny Farmhouse Apartment

The apartment is spacious, bright, and sunny. Full of charming and quirky old details like original windows, hardwood floors, and not many right angles. Definitely not a vanilla box. The furnishings are clean and comfortable and go with the farmhouse feel. Please note that the private staircase used to access the apartment is original to the house. It is steep by contemporary standards and the tread depths are all a little wonky.