Holiday rentals in Winchester

3 Bedroom Boston-area Gem

Your family will be 12 minutes to downtown in this exclusive Boston suburb! This is an older home (built in 1907!) It has the charms of a New England Victorian home. You can expect original hardwoods and wood detailing. The air-conditioning is supplied by window units, not central a/c. The Wedgmere stop in Winchester, on the Lowell train line goes into North Station in Boston. From North station, you take the green line to Boston University/Longwood Medical Area on the Subway, known as the "T"

House on A+ school area w/AC & W/D

Fabulous opportunity to stay in a prestigious school area & a historic residential town of Winchester, MA. It’s in a beautiful, quiet, & safe neighborhood on the west side of Winchester, MA, near Lexington, Arlington, & Woburn towns. Close to historic landmarks, restaurants, elementary school, highway, & public transportation. The in-law suite with a separate entrance is part of a single-family house on the back of an A+ elementary school. Relax with your friends & family at this peaceful place

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

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.

Dixie’s House, 1BD in Arlington

1 bedroom, family-friendly apartment in the quiet Morningside neighborhood of Arlington. Can sleep 5. Free driveway & off-street parking. King bed + queen sofa bed in living room, 1 full bath, coffee, microwave, toaster oven, foreman grill, rice maker & dishwasher. 1 mile from the bike path and short drive to Alewife MBTA and Davis Square. Young kids and dog live above (expect some noise). Bus route leads to Harvard Square nearby. Also close to Wright-Locke Farm with stunning fall hikes.

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.

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!

Spacious 1-BR apt+parking+laundry. 2nd BR option

Private 1-bedroom apartment suite near the Arlington/Winchester town line, Upper Mystic Lake, and conservation land. The bedroom is newly renovated and has a queen bed. Large living room. Small, functional kitchenette and eating area. Washer/dryer. Second bedroom available for additional fee. Parking in driveway for 1 car. it's a short walk to the 350 bus (~25-min ride to Alewife Red Line subway station.) Strong Wifi. TV with Roku (BYO streaming; no cable channels)