Vacation rentals in Milton

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and abundance on-street parking. Pet friendly!

Treetop Hideaway Close to Boston/ 2 bedrooms

Escape to our serene 3rd floor private suite & living room in quiet Milton neighborhood with beautiful gardens, 9 miles to Boston, close to public transit. This beautifully furnished retreat offers comfortable short/mid-term stay. Spacious master bedroom, king-size bed, built-in closets. 2nd bedroom for extra guests, Living area with electric fireplace, kitchenette & coffee maker. Luxury bathroom with 2 sinks - Washer & dryer in unit - WiFi. - Pets Welcome - Hosting World Cup Soccer 2026

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Woodland Retreat

Relax at this peaceful place to stay. Nestled in Canton and surrounded by tall trees, our home offers the feel of a private woodland retreat. A perfect escape from the city, while the yard is ideal for relaxing and outdoor barbecues. *Includes fully equipped kitchen and high-speed Wi-Fi. * Easy access to Boston and highways. Gillette Stadium (14 miles); TopGolf (4 miles); Shopping malls (5 miles); Commuter rail station (4 miles); Boston (20 miles). * Any events must be pre-approved.

Pet-Friendly House | Yard & Parking Near Boston

Spacious 1,800+ sq ft private main-level home in Milton with 2 bedrooms, King and Queen beds, two living rooms, full kitchen, dining area, bathroom with washer/dryer, and a large deck. Pet-friendly with approval, plus a large fenced yard and parking for 4 cars. Nearby bus service connects to Mattapan Station and the Red Line. Convenient to Milton Academy, Boston, Cambridge, Quincy, Blue Hills, hospitals, and shopping. Ideal for families, students, school-year stays, and longer stays.

Luxury Milton Home

Newly renovated home in a safe environment and proximity to Boston with easy access to public transportation, renowned museums and top universities. Inside, the open concept with the living room to dining room and the kitchen with an oversized center island. 3 master bedrooms with 3.5 bathrooms. The hallway has a laundry area and a half bath for your convenience. Outdoor included patio with dining area, grill, fire pit, and a mini golf. Many off street parking spaces available.

Guest Suite in Milton

This private suite features 2 comfortable bedrooms with cozy bedding. The suite includes a fully equipped kitchenette stocked with essentials for preparing meals. A clean, modern bathroom is supplied with fresh towels and basic toiletries for your convenience. It’s perfect for small families, couples, or business travelers. Enjoy complete privacy with your own separate entrance from the main house, allowing you to come and go as you please without disturbance.

Short Train 2 Boston, Luxury prvt unit w parking

Enjoy a comfortable stay in this private entrance, beautiful, newly renovated 1 bedroom apartment only a short 4 minute walk to Wollaston train station- 5 stops to downtown Boston. Convenient access to Boston by car (15-20min) as well. Full gut-renovation, open floor kitchen/dining room. Gorgeous bathroom. New HVAC system. W&D in unit. Off street parking spot right next to separate, private entrance. Great neighborhood, beautiful park across the street.

Spacious, Comfy Colonial minutes to Boston

Welcome to your World Cup home base. Spacious 4BR colonial minutes to Boston with easy access to Gillette Stadium. Comfortable for groups with central A/C, fast WiFi, off-street parking, patio, fire pit, and finished basement to relax after game day. About 25–35 min to Gillette, 15–20 min to Boston, and 20–25 min to Logan. Quiet neighborhood, easy check-in, and plenty of space to unwind. Great for families, friends, or fans—dates will go fast.

Your own cottage in the city

Whether you need to relax, be productive, or have a safe home base for your adventures, the Sowden cottage has you covered. Nestled near the heart of Roslindale, the cottage is a short walk to shopping and dining and is near easy transportation to every part of Boston. It's the perfect place to call home while you work, visit family, or experience the city we love. Whatever brings you to Boston, we look forward to welcoming you at the cottage!

Prestigious Milton Designer Home

Spacious designer home in one of Massachusetts’ most prestigious and safest towns. Located right off I-93, 15 min from Boston Downtown, and only 10 minutes from Blue Hills Reservation for hiking, skiing, and year-round outdoor activities. With 3 large bedrooms, 1.5 baths, and room for up to 12 guests plus free parking for 4 cars, this home offers comfort, style, and convenience for families and groups.