Holiday rentals in Horn Pond Mountain

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.

Lovely 5Bed • Super Clean • Nature & City Life

Charming, super-clean 5-bed in 3 levels of a house, surrounded by nature in the city. Enjoy the best of both worlds in this cozy, spotless space beside 10+ acres of forest — a true retreat in an urban setting. Only neighbor is the unit below in the lower level. Includes everything shown in the photos: living, dining, and kitchen, 2.5 bathrooms, and 5 comfortable bedrooms. 3 on site parking spaces. Walk to Horn Pond for waterfront strolls or hikes. Great food and shops in Woburn and Winchester.

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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.

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.

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!

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.

Quiet 2BD Single-Family, Parking, No Shared Walls!

Enjoy the rare comfort and privacy of a newly renovated detached single-family home—no shared walls, no neighbors above or below or sides, just a quiet space all to yourself! Located just 20 min from Boston with easy access to I-93, I-95, and Route 3. Walk to Woburn Center’s restaurants, cafés, and shops, and enjoy quick access to Lahey and Winchester hospitals. Perfect for school visits, business travel, or family stays. Private 2-car driveway parking is included right next to the house.

Modern Grand Retreat |5B5B |Brand New Luxury House

Escape to spacious, comfort and style in this stunning modern 6B5B home. Nestled on a quiet street near Whipple Hill and the Minuteman Bikeway, this professionally designed home offers high-end finishes, abundant natural light, and all the amenities you need for a relaxing stay. Enjoy a spacious open-concept layout with sunny living and dining areas, a chef’s kitchen with stainless steel appliances and oversized island, and a private backyard with a furnished patio for outdoor dining.

Private studio in a quiet and nice area

Private Studio located in a great and quiet neighborhood in Arlington, steps to McClennan Park. Kitchen with electric cook-top (no oven), built-in microwave, mini fridge, dishwasher. Sofa-Bed (queen size). Large Desk. A small private patio under the deck of the main house (where we are living). Parking space available on Thesda street (along the house). 8 minutes drive to Downtown Arlington, 25 minutes to Downtown Boston. Free wifi & TV available. Available upon request: Bikes, iron.

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!

3 Bedroom 2nd Floor Unit - commute to Boston

This private second-floor unit is part of a single-family home and features three bedrooms with separate access via an outdoor staircase. The unit is separate from the host’s first-floor space, providing guests with privacy. It includes two bedrooms with queen beds, one bedroom with a double bed, a spacious bathroom, and a compact kitchenette/breakfast nook with basic amenities. Parking is available in the driveway for up to two standard-size cars.