Holiday rentals in Southampton

Briggs Cove: Private & Lovely 1st floor apartment

Your family will be close to everything when you stay at this centrally-located home. Walk to terrific restaurants, comic and book stores, gift shops and enjoy an award winning scoop of ice cream on the boardwalk at Nashawannuck pond! Whether you are looking for a hiking trail, a place to put your kayak in, or a great dining experience, this location has what you are looking for. Enjoy your time in western Massachusetts, at your own pace. Then, relax in the comfort of your own private oasis.

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.

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.

The Floating Library: private hiker's hideaway

Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

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.

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Goreytastic Private ApARTment @ the EMC

Self-contained completely private in-law Edward Gorey inspired artistic apartment at the Easthampton Music Conservatory (right off the Williston Campus.) Romantic, campy, silly, spooky, quirky space with Edward Gorey and original artwork, a micro library including classic TV shows and popular B movies, vintage Nintendo system & oversized beanbags for Nintendo aficionados of all ages. To be clear: entirely self-contained space. Private EVERYTHING. NO shared spaces.

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.