House holiday rentals in Massachusetts

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Family · Location · Check-in

Lake Front Home Sleeps 6-8 on a private Peninsula!

Stunning year-round waterfront home on its own private peninsula—sleeps 6–8 with 3BR/2BA, a spacious living room with sliders to a wraparound deck, and a heated sun porch offering panoramic lake views. Nearly every window overlooks the water. Outside, enjoy a private dock, new stone patio & firepit, small beach area, kayaks, canoe, and rowboat. Perfect for families, couples, or a friends’ getaway. See walkthrough videos at on YouTube @CedarLakeCottage Summer: 4-night min | Holidays: 3-night min

Family · Value · Bathroom

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

Location · Value · Walkability

Cozy en suite w/ high ceilings

 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

Value · Family · Long stay

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Value · Location · Access

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Value · Family · Comfort

Beautiful & Historic New England Colonial c.1780

The Zadock Taft House is the quintessential historic New England post & beam colonial home & listed on the National Registry of Historic Places. The house is fully climate controlled and includes 3 bedrooms, a cozy “family parlor” providing a perfect to relax and watch tv, and our wonderfully restored “tea room” and “flower room!” We invite guests to step back in time while enjoying modern day amenities! Gillette Stadium-30min. Boston-50min. Providence-25min. Newport-60min. Worcester-25min.

Location · Value · Parking

Lakefront House Boston, Plymouth, Cape Cod

Directly on the lake, with spectacular year round views. Perfect for a couple’s getaway or a family vacation. Its our family lake home where many special memories have been made & more are waiting! Home is about 15 minutes to historic Plymouth, 35 minutes to Boston, 20 minutes to coastal beaches, 40 mins to Cape Cod, 8 mins to Fieldstone show park & just 1 mile from the MBTA Halifax commuter rail station-takes you right into Boston or just stay & enjoy the lake. Private water access.

Family · Location · Hiking

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Family · Location · Amenities

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Value · Location · Quiet

An 18th century farmhouse

Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.

Location · Value · Nearby

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Location · Family · Decor