Pet-friendly holiday rentals in Middlesex County

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Cozy en suite w/ high ceilings

 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Lots of 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. 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. Safe walkable neighborhood.

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Vaughn Hill Hideaway & Sauna

Tucked into the slope of Vaughn Hill on 3 wooded acres, the entire lower level of our home is yours to enjoy. Cozy 2-bedroom unit with “the BEST BEDS at an Air BNB ever!" to quote a guest. Visit Nashoba Valley Winery, get coffee at Harvard General Store, go apple-picking at a local orchard, or hike Vaughn Hill trails. *Wood-fired backyard sauna available by request with $20 firing fee *Well-behaved dogs (non-destructive, house-broken) welcome! Sorry - no cats, due to prior experiences.

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

#9 Modern Home 15 min to Boston w/ Yard & Parking

Stay in this stylish 2-story home with 3 Comfy Bedrooms + 1.5 Baths! Ideal for families or groups, it comfortably fits 6+ guests. Enjoy a fully stocked kitchen, dedicated workspace, and a private backyard with a BBQ & a fire pit. Perfectly located for exploring Boston, Cambridge, and Salem with free private parking. Your memorable stay with experienced Superhosts awaits! 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🌆 Easy Access to Local Attractions

Conveniently Located Private Garden Apartment

Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

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.

Spacious Two Bedroom Apartment

Private and clean renovated 2 bedroom apartment in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 6 comfortably in 2 queen beds and 1 futon. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27. Close to many colleges and MetroWest office parks.

Private Studio w/ Loft Center Historic Carlisle

Charming private studio in the heart of Carlisle, perfect for 2 adults (up to 4 guests). Completely separate with no shared spaces. Close to Routes 128, 495, 35min to Boston, 10 min to historic Concord. Outdoor lovers enjoy nearby hiking, biking, and Great Brook Farm State Park. Easy access to Lowell, Nashoba Valley Ski Area, shops, and restaurants.