Guest house holiday rentals in Hampshire County

Sage House:stylish guesthouse near Noho/E’ton

Designed by travelers, this custom detached guesthouse is unique in the area-modern, private,bright,uncluttered. No glade plug-ins ;) 1mi to dwtn E’ton, 5mi to Smith/noho. Private deck/ yard. Separate driveway. full kitchen. W/D in unit, cotton sheets, quiet neighborhood, helix queen mattresses. Coffee. Plenty of work space. Heated tile in bathroom! Epic morning sun on balcony. No parties/noise! Shop underneath may be in use M-F 9-5. read full description and rules before booking, or inquire.

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!

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!

Newly Constructed Guest House with Pool

200 sf guest house adjacent to our home. Space complete w/ wifi, heat, A/C + ceiling fan. QUEEN size sleeper sofa , full size mattress in sleeping loft, kitchenette w/sink + mini fridge, HALF bath, OUTDOOR shower, private patio and in-ground pool. Outdoor lighting allows for nighttime enjoyment of guest house, pool and enclosed yard. Walking distance to Florence ctr, 2 mi from downtown Northampton. THIS SPACE IS MORE COMFORTABLE FOR 2 PEOPLE - but there is enough sleeping space for 3.

Tiny Home close to amenities. Monthly Available!

Welcome to the tiny home! We're located in the woods nestled behind the lot surrounded by mature plants and trees. Enjoy your peaceful retreat with the comforts of home, including your own private bathroom & kitchenette. The cozy twin bed and sofa bed provide a comfortable & restful night's sleep. The convertible coffee table & expandable dining table create a flexible space for dining & working. If you want privacy and comfort rolled into one, you'll definitely love our tiny home.

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.

The Robert Frost Trail Lodge

Nestled along the Robert Frost Trail, this charming guest house, an ADU attached to a private house blends rustic appeal with modern comfort. Surrounded by a serene wood, it boasts a private trail to the Robert Frost Trail. Enjoy stunning panoramic views, just 10 minutes from U-Mass and Amherst College, and 15 minutes from Mount Holyoke, Smith, and Hampshire. This guest house offers a perfect connection between nature and warm vitality.

Newly built loft

Come relax and enjoy a getaway in our spacious and serene loft. The space is a one room, open-floor plan retreat with its own private entrance above the detached garage on our property. The bed is a pull out couch as pictured in the listing. The charming downtown of our beloved Easthampton is a little over 1 mile easy walk where you will find many restaurants, bakeries and shops to explore.

Cozy get-away!

This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing, TV-free space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!

Zen Black House near Smith College, Mill River

LGBTQ+ friendly. Escape to the Zen Black House, striking, modern asymmetrical house and inspiring space surrounded by lush nature in a lovely historic neighborhood less than a mile walk down the Mill River Trail or few minutes drive down Elm Street to downtown Northampton. DOGS WELCOME! Sleeps 6 but note it's open concept living. This earth friendly house is fossil fuel free.

Country Cabin

Lovely private country setting, air conditioner. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. The space is for 2 adults but I'm flexible, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Amherst Area Studio Apartment

Convenient location on quiet side road near Amherst, Hampshire, and UMass. Easy commute to Smith and Mt. Holyoke. Unique 2nd floor open studio space with 1 single and 1 dble bed, a sofa and chair, a dining nook with a small kitchenette + full bath. Bathroom is on first floor but studio is on second floor. Public beach is available June 24 and is steps away!