Holiday rentals in Chesterfield

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.

Private Studio for a Sweet Getaway!

A cozy, comfortable, studio flat with ready access to local music venues and restaurants. Downtown Northampton is 15 mins by car or a 1/2 hr bike ride. We abut the bike path and there's a Valley Bike Share kiosk nearby. Ideal overnight spot for visiting Smith and other area colleges or for attending workshops at Snow farm. Easy day trips the Berkshires. Plenty of area hiking! Perfect personal retreat spot! I accept dogs on a case by case basis, small dogs preferred and I cannot accept cats.

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.

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

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.

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Warm & Stylish Apartment w/laundry - walk to DT

Warm and stylish 1 bedroom apartment with private garden entrance located steps from downtown Northampton. Newly refinished with a comfortable queen bed, sleeper sectional and luxury linens. It has a fully functional kitchen, bathroom, living room with a flatscreen, Roku and high-speed wifi as well as a washer/dryer in the unit-- perfect for a staycation or for a relaxed homestay for your remote work. Walk 15 mins to restaurants downtown, 20 mins to Smith College and 2 to the bike path.

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

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.

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!