Holiday houses in Winchester

Winchester Apartment on Greenway

Updated apartment with hardwood floors, full kitchen and washer/dryer, next to Davidson Park, Tri-Community Greenway and the Community sport complex. A wonderful short walk down the Greenway takes you to Leonard Pond for tennis, pickleball, soccer or frisbee. A 20-minute walk down the Greenway takes you to Winchester Center for restaurants, shops and train to Boston. Or walk four blocks east to explore the 2,000-acre Middlesex Fells Reservation. Route 93 access is less than a 5-minute drive.

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.

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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!

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.

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 + extra twin. 1 full bath, kitchenette with dishwasher (No Oven or Cooktop). NEW washer/dryer combo! 1 mile from the bike path and short drive to Alewife/Davis T stations. Young kids and dog live above (expect some noise). Bus route to Harvard Square nearby. Also close to Wright-Locke Farm with stunning fall hikes.

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!

New Construction En Suite

Accommodations by Veteran Airbnb Hosts, we present An En suite in a new construction townhome. On the fringe of the suburbs, This special place is close to everything, making it easy to plan your visit. You have your own Entrance/exit into your space. 12 1/2 foot High cielings in your dedicated Level of the building gives this space a very West Coast feel. Walk out to your own Private patio for dining or relaxing as well as some shared greenspace to walk your fury friend.

3 Bedroom Boston-area Gem

Your family will be 12 minutes to downtown in this exclusive Boston suburb! Brand new kitchen renovation in Dec 2025! 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.

Entire guest suite in Stoneham

Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.

Contemporary Apartment in Beautiful Historic Home

Stunning, newly renovated 800sq ft one bedroom apartment. Stylishly decorated with many modern amenities. Located on the first floor level of a historical Grand Victorian home dating to 1900. Gorgeous original details throughout the apartment and high ceilings. A perfect representation of a classic Boston period home. Find style and comfort in this amazing new apartment!