
Holiday rentals in Hampshire County
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Top-rated holiday rentals in Hampshire County
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

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.

Luxurious and Sunny Bedroom Suite!
Luxurious and sunny suite with private bath, separate entrance, Tv/sitting room, reading nook, desk/work area, and coffee bar. 6 blocks to town, and beautiful views of Skinner Mt. Decorated with handcrafted wood furniture by one of Northampton's most recognized furniture makers. Private patio, large backyard with pick-your-own raspberries and blueberries. The suite has a private parking space, and is conveniently located near the bike path, and route 91. Come relax, and explore Northampton.

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!

1840 restored beauty in the best downtown location
Newly restored 2nd-floor apartment in 175-year-old home 2 blocks from Amherst Cinema & steps to everything this vibrant downtown has to offer. Walking distance to Amherst College and UMass. This home retains the character of days gone by, yet sparkles with new wood floors, modern bathroom & new appliances. Original wood-paneled entry hallway & exposed beams throughout. Antique furnishings, historic wall decor, and a sunny kitchen with built-in reclaimed wood bar. Small balcony w seating for 2.

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.

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.

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.

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!

Private Farm Studio Apartment
Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes from Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private studio apartment is on the first level of our rustic farmhouse and offers a queen bed, kitchenette, living room, and bathroom. A sofabed is available for an extra $20 fee, please request this upon booking.

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.
Popular amenities for Hampshire County holiday rentals
Other great holiday rentals in Hampshire County

Historic Williams House

Cozy cottage on small intown farm.

Spacious, Sunny* Woodland Retreat

Quiet spot near downtown & Smith College

Button’s Modern Luxury Walkup DT

Sunderland house - 5 College area

Studio Apartment

The Walnut Apartment
Destinations to explore
- Family-friendly rentals Hampshire County
- Rentals with lake access Hampshire County
- Rentals with a fireplace Hampshire County
- House rentals Hampshire County
- Rentals with an EV charger Hampshire County
- Rentals with a patio Hampshire County
- Private suite rentals Hampshire County
- Rentals with a firepit Hampshire County
- Rentals with a kayak Hampshire County
- Guest house rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Flat rentals Hampshire County
- Rentals with pools Hampshire County
- Smoking-friendly rentals Hampshire County
- Rentals with outdoor seating Hampshire County
- Rentals with a washing machine and dryer Hampshire County
- Pet-friendly rentals Hampshire County
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Clark University
- Connecticut Science Center
- Dcu Center
- Mount Monadnock
- University of Connecticut
- Massachusetts Museum of Contemporary Art
- Smith College
- Mount Greylock




