Holiday houses in Milton

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Top-rated holiday rentals in Milton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright and airy room features a comfortable bed adorned with colorful bedding. Two wooden desks with chairs are positioned thoughtfully, along with various seating options. Natural light filters through a window, accentuating the room's warm wood flooring and blue walls.
Guest suite in Boston
4.9 out of 5 average rating, 178 reviews

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!

Guest favourite
A modern dining area features a glass-top table surrounded by four black chairs, positioned over a decorative rug. A colorful wall art piece is displayed nearby, and an electric fireplace adds warmth to the space. Light-colored walls and flooring enhance the ambiance.
Apartment in Quincy
4.96 out of 5 average rating, 117 reviews

“Very Modern Apartment” Dedicated Driveway Parking

Whether you are just getting away for the weekend or looking for an extended stay, we are committed to creating a comfortable experience. Professionally cleaned & sanitized Great customer service High quality linens and towels. Very spacious 1100 sq ft 2 bedrooms and 1 bath unit with high ceiling. Each bedroom features a queen bed with foldable twin beds. Fully stocked with everything you might need for longer comfortable stay. Located in a very nice residential area.Dedicated driveway parking

Guest favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.94 out of 5 average rating, 144 reviews

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!

Top Guest favourite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon
4.95 out of 5 average rating, 216 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

Guest favourite
The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.
Home in Hyde Park
4.91 out of 5 average rating, 374 reviews

~*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

Guest favourite
A spacious outdoor area features a mini golf setup with several flags on vibrant green turf. A dining table is nestled under an umbrella, surrounded by well-kept landscaping and trees. A grill is visible, and a stone seating area adds to the outdoor charm.
Apartment in Milton
4.94 out of 5 average rating, 17 reviews

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.

Top Guest favourite
An open kitchen is paired with a comfortable living area, featuring light hardwood floors. The kitchen includes modern appliances and a spacious island with seating. A neutral-colored sofa and coffee table create a relaxed ambiance, with plants adding a touch of greenery in the background.
Condo in Boston
4.95 out of 5 average rating, 301 reviews

3-Bedroom Apt (7W2) 20-Minuite To Downtown Boston

Perfect for families and groups, this clean, newly renovated 3-level home has 1 King and 2 full size bedrooms and sofa sleeper in living room 2.5 bathrooms (including a half bath on the main floor), and thoughtful touches like snacks, coffee, wine, chargers, travel crib, and fast Wi-Fi. Located in an authentic Boston neighborhood ~20–30 min from downtown by car or transit. Expect lively local character, easy access to public transport, and normal city sounds.

Top Guest favourite
Apartment in Milton
5 out of 5 average rating, 18 reviews

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.

Top Guest favourite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 285 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Guest favourite
A modern kitchen features grey cabinetry and quartz countertops with veining. Full-sized appliances, including a refrigerator and gas stove, are present. A pendant light hangs above a spacious kitchen island, while a window allows natural light to brighten the area. Decorative elements are present on the counter.
Apartment in Milton
4.93 out of 5 average rating, 165 reviews

Milton - Immaculate & renovated 3 bed 2 .5 bath!

Welcome to our attached duplex family home. We recently renovated this home from top to bottom with brand new finishes and custom design. Our home has three large bedrooms with two full bathrooms with two living room areas that are a great fit for your family and friends. Some key features of the home are hardwood floors, quartz counter, bright recessed lights, and large yard for outdoor play.

Guest favourite
An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.
Home in Jamaica Plain
4.91 out of 5 average rating, 171 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Bright and sunny 2-bedroom retreat with a fully equipped kitchen, spacious bath with rain shower and tub, and TVs in each room. Enjoy fresh coffee daily with espresso maker, milk steamer, and grinder provided. Including a blender..A selection of teas .WiFi and off-street parking included. Private, peaceful, and filled with natural light—perfect for relaxing mornings and cozy evenings!

Top Guest favourite
A pathway lined with brick leads to a cozy cottage with maroon siding, framed by lush greenery. A seating area with chairs is positioned on a well-maintained lawn, inviting relaxation on a sunny day. Tall trees provide shade, enhancing the tranquil ambiance.
Barn in Nahant
5 out of 5 average rating, 167 reviews

Entire Beach-Town Cottage, Barn Charm, near Boston

A nicely renovated, old barn, fully furnished, where contemporary style meets barn-charm. Located in a quiet neighborhood with private yard and only minutes to the beach. Parking on premises. The ideal location for a short getaway with family or friends or to unwind after a long day at work. Only 25' from downtown Boston and other North Shore towns with restaurants and bars.

Popular amenities for Milton holiday rentals

When is the best time to visit Milton?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Milton?

    Milton has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Milton?

    Experience the best of Milton with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Milton?

    Four-legged friends are welcome in Milton. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Milton?

    Yes! Work meets play with ease at over 80 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Milton?

    Make yourself at home in Milton by choosing from our most frequently booked neighborhoods. We have over 310 vacation rentals in Stony Brook - Cleary Square, over 2,580 vacation rentals in Montclair, and over 310 vacation rentals in Hyde Park.

  • Do hotel rentals in Milton have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Milton have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Milton have wifi?

    Absolutely! We offer over 60 apartment rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Milton have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Milton. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Milton?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with free parking, over 60 homes with wifi, over 60 homes with a kitchen, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Milton

  • Total holiday rentals

    Explore 160 holiday rentals in Milton

  • Nightly prices starting at

    Milton holiday rentals start at $41 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Milton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Milton rentals

  • 4.7 Average rating

    Milton stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Milton's top spots, include Milton Station, Central Avenue Station, and Butler Station

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