Holiday rentals in Winchester

Charming Waterfront Cottage Near Cambridge/Boston

Delightful 1-bedroom guest cottage in Arlington with picturesque waterfront views and cozy interiors. Tucked away on Spy Pond, the cottage offers a peaceful retreat and a short drive to Cambridge (10 min to Harvard Square), Boston (20-25 minutes to Logan Airport), and Harvard, MIT, Tufts, BU. Comfortable furnishings and an abundance of windows overlooking the water create a bright and calming backdrop for your stay. Enjoy getting away from it all, while being close to everything you might need!

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

The Little House - a historic New England cottage.

This old fashioned New England cottage in a pocket of wooded suburbs just 9 miles from Logan Airport. 4 miles from Lexington Green where the revolutionary war began. Inside the 128 beltway, its an oasis of calm in the heart of Metro Boston. Keyless entry for easy check in. A highly sought location for ice skating in winter. In summer, enjoy a chorus of frogs every night & ample wildlife sightings. Your hosts live next door, in a quiet, family neighborhood. Kids are welcome, parties are not.

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

Warm home in Lexington, walk to town, nature trail

A newly built in-law apartment, located in the historical Lexington, is welcoming travelers home. Located in a safe and friendly community, the apartment is convenient to town center, Boston, restaurants, shops, tourist spots, and Lower Vine Brook forest trail (1 min walk)! The apartment follows enhanced cleaning protocol, with thorough ventilation and disinfecting. The HVAC system is private. Checkin and checkout are easy and no-contact. Registered with the town of Lexington: STML-21-2.

Relaxing and Comfortable Home Away From Home

Privacy and comfort in complete lower level of this home. Private entrance and no shared space all within 5 minutes of shopping/restaurants and major highways. The space features a large kitchen w/dining area for 4pp, 1 bedroom with queen sized bed , living room with 65 inch tv with full cable. 1 full Bathroom with shower and tub. Washer and dryer are also included. Professionally maintained and enclosed backyard and patio area for outdoor seating.Full sized bed in the bonus room.

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance. It's on the first floor so there are no stairs!