Vacation rentals in Milton

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Top-rated vacation rentals in Milton

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

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Top guest favorite
A welcoming living room features a ceiling fan and natural light from multiple windows. A comfortable sofa is positioned near a wooden cart, while a flat-screen TV is mounted on the wall. The staircase leads to an upper level, and an opening reveals a bright dining area.
Home in Arlington
4.97 out of 5 average rating, 109 reviews

Sophisticated, bright, and cheerful 2 story home

Enjoy the privacy of your own 2 story home! Nestled in a peaceful suburban neighborhood mere blocks from quaint eateries and shopping, this sun-drenched home features off-street parking (2 cars), 2 queen beds, wifi, Netflix, modern appliances (including laundry), and small work space. Easy access to Boston, top hospitals, & 21 colleges & universities including Harvard, MIT, BU, & BC via train. A short walk from train station and close to 2 major highways this hidden gem truly is a revelation!

Top guest favorite
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 Dorchester
4.9 out of 5 average rating, 172 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!

Top guest favorite
A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.
Guest suite in Ashmont
4.96 out of 5 average rating, 269 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Guest favorite
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 favorite
Apartment in North Quincy
4.92 out of 5 average rating, 172 reviews

Beach Home next to Boston & T, King Bed, Park Free

Enjoy a comfortable stay in this beautiful, newly renovated 3 bed 2 bath apartment only 150 yards to the beach and convenient access to Boston by car (15-25min) or public transport (30-45min). It's a spacious 1300 sqft, was just fully remodeled, retains plenty of character and boasts loads of windows and light. Recharge from your trip in style with a fully equipped kitchen, three new comfortable beds, 55" TV, sofa, work & dining area, new bathrooms, walk-in closet, and free off-street parking.

Top guest favorite
A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.
Boat in Charlestown
4.95 out of 5 average rating, 143 reviews

2BR Spacious Yacht - Heat & AC- On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

Top guest favorite
The living room features light-colored sofas and a coffee table placed on a warm area rug. Bright natural light enters through several windows, illuminating the space. A wall-mounted TV is visible, and a stylish coat rack adds a modern touch.
Home in Braintree
4.95 out of 5 average rating, 126 reviews

Near Boston w/ parking & deck, 3-bedroom home

Bright and cozy space located in Braintree Center, just 10-miles outside of Boston. Our home is an ideal location for families, friends, business travelers, and even wedding parties looking for more space, while also enjoying the proximity to Boston, Logan Airport, and more! Have a wedding, event, or want to see a sunset view of the Boston skyline? Granite Links Golf Course is 4 miles away! Looking to see a concert or Patriots Game at Gillette stadium? Arrive there in just 25 minutes.

Top guest favorite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Apartment in Newton Highlands
5 out of 5 average rating, 104 reviews

Inn at Newton Highlands, Suite 2, Apartment-Hotel

This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

Guest favorite
A spacious living area features large windows offering views of greenery. A comfortable queen bed is set against one wall, while a pullout sofa sits opposite. Light-colored curtains frame the windows, and a stylish lamp is placed beside a round table.
Guest suite in Roslindale
4.9 out of 5 average rating, 213 reviews

Cozy Renovated Suite w/Free St Parking near Train

Newly renovated in-law suite located in the charming Roslindale neighborhood of Boston. A short walk from West Roxbury Center, Roslindale Village's shops and restaurants, and Bellevue commuter rail stop which gets you to Back Bay in 15 mins (or 20 Min Uber/drive). Features include a private entrance kitchenette, bathroom, large quiet back yard with patio and fire pit (avail Apr-Oct). Perfect for weekend getaways, working/commuting to Boston, or visiting friends and family!

Guest favorite
A spacious bedroom is depicted, featuring a king-size bed dressed in crisp white bedding. Warm light emanates from two bedside lamps, illuminating simple wooden nightstands. Dark window shades frame the windows, contributing to a calm and restful environment.
Apartment in Roslindale
4.92 out of 5 average rating, 125 reviews

Modern 1BR apt in Boston’s Roslindale Village

This place is on the 3rd floor of our newly renovated home in Boston's Roslindale, which is about 6 miles away from downtown (please look up the neighborhood to have a clear idea where it is). Our place is close to restaurants & bars in Rozzy Village and West Roxbury. There is a connection via bus at the corner to the subway at the Forest Hills Orange Line T-stop that will get you to downtown in about 30 min, and there is commuter rail in Roslindale Village.

Top guest favorite
The open kitchen and dining area feature a round dining table surrounded by four chairs. Natural light fills the space through large windows, illuminating the glossy stained hardwood floors. A decorative plant adds a touch of greenery, enhancing the overall inviting ambiance.
Apartment in Wollaston
4.96 out of 5 average rating, 211 reviews

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.

Top guest favorite
A welcoming living area features a dark sofa with a plush throw pillow, complemented by a glass coffee table and decorative area rug. In the background, a console table holds a bowl and art pieces. A floor lamp provides soft lighting, enhancing the space's comfort.
Condo in Jamaica Plain
4.9 out of 5 average rating, 106 reviews

Leafy & Tranquil, Artist house. Easy access Boston

Call it home! Enjoy this spacious two-bedroom apartment on a tranquil side street of Jamaica Plain. Apartment is furnished and has full kitchen. Two blocks to the Southwest Corridor where you'll find bike and running trails and the T transit. Discover the charms of Jamaica Plain: its locally-owned businesses, small breweries, cute coffee shops, art studios, and lots of nice outdoor space for recreation and relaxation.

Popular amenities for Milton vacation rentals

When is the best time to visit Milton?

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Avg. priceR1,976 ZARR1,942 ZARR2,111 ZARR2,348 ZARR2,348 ZARR2,534 ZARR2,483 ZARR2,567 ZARR2,415 ZARR2,534 ZARR2,415 ZARR2,246 ZAR
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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 apartment rentals in Milton?

    Experience the best of Milton with our apartment 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 90 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 2,650 vacation rentals in Montclair, and over 310 vacation rentals in Hyde Park.

  • Do house rentals in Milton have air conditioning?

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

  • Do apartment rentals in Milton have a kitchen?

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

  • Do house rentals in Milton have wifi?

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

  • Do apartment rentals in Milton have free parking?

    Absolutely! We offer over 50 apartment 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 a kitchen, over 60 homes with wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Milton

  • Total vacation rentals

    Explore 160 vacation rentals in Milton

  • Nightly prices starting at

    Milton vacation rentals start at R507 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 5,130 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Milton vacation 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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