Guest house holiday rentals in Pioneer Valley

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!

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Coziest Suite between Berkshire East and Mt. Snow

High Value in the countryside Between Mt.Snow &Berkshire East Hilltop near Shelburne Falls Stone fireplace/post and beam Host on site as needed Close to DA &NMH Elegant minimal decor 12 acres with views Near excellent restaurants The most comfortable king Leesa bed & Double 4 poster bed with High end cotton/linen bedding Spa robes Kitchenette w/ fridge air fryer toaster oven microwave Coffee/tea/baked goods Complete privacy tiny library house Large smart tv Bonfire State forest 1/2 mile away

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!

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.

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

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!

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Peaceful forest cottage getaway

Cozy one bedroom cottage with kitchen overlooking a forest meadow. Walking paths along a lovely brook. Owner lives in a separate residence 100 feet up the hill and may be seen outside in the meadow, garden or shared driveway. There is a pull out queen sofa bed in the living room in addition to the queen bed in the bedroom, although the cottage is most comfortable for 1 or 2 guests.

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.