
Holiday rentals in Milton
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Top-rated holiday rentals in Milton
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

“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

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!

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.

~*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

The Raven!
Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

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.

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.

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.

Home in Boston/Milton
This newly renovated property boasts an open floor plan, offering a modern design with brand-new appliances. Located in a peaceful neighborhood, it provides the perfect balance of tranquil living and convenient access to all that Boston has to offer. Just minutes from Downtown Boston, Blue Hills Reservation, Milton Academy, and local beaches, it's an ideal spot for both relaxation and adventure.

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.

Luxury, Location, Privacy. Walk to train. Boston
Luxury. Convenient. Short walk to train. 5 stops to South Station, The main station in Boston. Short walk to stores, restaurants. All brand new. Full gut renovation. Parking spot right outside your private entrance. This is a true getaway. Washer and Dryer also in unit. Beautiful park right across the street. One bedroom unit with a pullout couch in living room.
Popular amenities for Milton holiday rentals
Other great holiday rentals in Milton

Charming 3BDR Boston Stay Garage + EV + Pool Table

Retreat Milton/Boston line (transit close) Pets

South Shore Beachfront Home *Newly Renovated

Newly Renovated 4BR, 2BA – Near Gillette & Boston

Milton 3bd Condo - Welcome Home! 2nd floor

Charming Milton Escape -Blue Hills Views

5 min walk to T train, 20 min to Downtown Boston

Elegant 4BR Retreat | Yard & Parking | Dedham
When is the best time to visit Milton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £86 | £85 | £92 | £103 | £103 | £111 | £109 | £112 | £106 | £111 | £106 | £98 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
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 $40 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 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 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 House Rentals in Milton?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with free parking, over 60 homes with wifi, over 60 homes with air conditioning, over 50 homes with a kitchen, 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 £22 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
160 of Milton holiday rentals include wifi 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
Destinations to explore
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Northeastern University
- Freedom Trail
- Boston Convention and Exhibition Center
- Gillette Stadium
- MIT Museum
- East Sandwich Beach
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Quincy Market
- Museum of Fine Arts
- Roxbury Crossing Station
- Onset Beach
- Prudential Center




