Milton holiday rentals

We found 2,647 holiday rentals — enter your dates for availability
Discover a selection of 15 homes, 17 apartments and other holiday rentals in Milton that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a fireplace. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Milton

Showing deals for:25 Dec - 1 Jan

Dining
Private kitchen
Interior
Interior
Exceptional
(98 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
AU$16,953
for 7 nights, 1 home
AU$2,422 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Interior
Exterior detail
Private kitchen
Interior
Exceptional
(6 reviews)

Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17

Newton

9% off
AU$25,499
for 7 nights, 1 home
AU$3,643 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
AU$7,983
for 7 nights, 1 home
AU$1,140 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Gracious staircase access to Third Floor
Marina
View of waterfront from Third Floor Suite Living Room
Patio garden
Exceptional
(98 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,917
for 7 nights, 1 room
AU$417 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Private kitchen
Living area
Interior
Room
Exceptional
(9 reviews)

Ocean front Studio across from beach

Hull

8% off
AU$3,248
for 7 nights, 1 home
AU$464 per night
includes taxes & fees
Ocean front Studio across from beach
Private kitchen
Terrace/patio
Exterior detail
Room
Exceptional
(34 reviews)

Lovely Studio Walk to Wellesley and Babson College

Wellesley

8% off
AU$3,074
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
Lovely Studio Walk to Wellesley and Babson College
Walkway from waterfront to my home at top of stairs
View of Spinnaker Island and water from Master Bedroom Suite
Portion of garden surrounding my home
Staircase from waterfront to my home
Excellent
(48 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
AU$2,699
for 7 nights, 1 room
AU$386 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Sitting room
Property grounds
Kitchen
Exterior detail
Exceptional
(21 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

8% off
AU$4,746
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Outdoor dining
Living area
Private kitchen
Living area
Exceptional
(44 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,725
for 7 nights, 1 apartment
AU$1,104 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Bathroom
Interior
Interior
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,943
for 7 nights, 1 home
AU$849 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Private kitchen
Living area
Interior
Dining
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
AU$5,852
for 7 nights, 1 apartment
AU$836 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Property grounds
Interior
Interior
Living area
Exceptional
(20 reviews)

Direct Ocean Front Condo with large wrap around balcony

Hull

8% off
AU$3,990
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
Direct Ocean Front Condo with large wrap around balcony
Property grounds
Private kitchen
Interior
Living area
Wonderful
(24 reviews)

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Boston

8% off
AU$5,713
for 7 nights, 1 apartment
AU$816 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Private kitchen
Spacious 4 BR home for groups. Perfect for relaxing and gathering together
Outdoor dining
Dining
Exceptional
(12 reviews)

4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train

Boston

8% off
AU$7,434
for 7 nights, 1 apartment
AU$1,062 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Bedroom #1
Backyard
Stainless steel kitchen appliances. (Old Table)
BPL Egleston Square library branch
Exceptional
(71 reviews)

2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway

Boston

5% off
AU$3,542
for 7 nights, 1 apartment
AU$506 per night
includes taxes & fees
2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway
Interior
Interior
Private kitchen
Room
Excellent
(7 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
AU$7,038
for 7 nights, 1 apartment
AU$1,005 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Dining
Living area
Interior
Room
Exceptional
(78 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
AU$1,413
for 7 nights, 1 room
AU$202 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Private kitchen
Interior
Private kitchen
Interior
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,641
for 7 nights, 1 apartment
AU$806 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Overview
Private kitchen
Room
Living area
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
AU$4,200
for 7 nights, 1 apartment
AU$600 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Dining
Room
Living area
Interior
Exceptional
(45 reviews)

A Cozy 5BR Apartment near Harvard Square and MIT

Cambridge

7% off
AU$5,688
for 7 nights, 1 apartment
AU$813 per night
includes taxes & fees
A Cozy 5BR Apartment near Harvard Square and MIT
Room
Dining
Living area
Living area
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,082
for 7 nights, 1 apartment
AU$726 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Private kitchen
Room
Terrace/patio
Living area
Exceptional
(25 reviews)

Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass

Cambridge

16% off
AU$4,847
for 7 nights, 1 home
AU$692 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Open Kitchen/Dining Area
Living area
Entrance/steps to apartment. Please note, steps required
Located on floor 2 of a classic Boston 1860's Rowhouse
Exceptional
(90 reviews)

Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!

Boston

8% off
AU$2,315
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Room
Interior
Private kitchen
Outdoor dining
Exceptional
(30 reviews)

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Boston

7% off
AU$2,526
for 7 nights, 1 apartment
AU$361 per night
includes taxes & fees
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

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Delight in the natural landscape of Milton

The wildlife and other outdoor surroundings create an inviting atmosphere in Milton. Well known for its hiking, shopping and restaurants, this scenic city won't disappoint. Fenway Park and Gillette Stadium are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Milton

Do you want to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that Milton has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (10.1 mi / 16.2 km)
  • Granite Links Golf Club (1 mi / 1.7 km)
  • Blue Hills Reservation (2.6 mi / 4.3 km)
  • Blue Hills Ski Area (3.5 mi / 5.6 km)
  • Franklin Park Zoo (4 mi / 6.5 km)
  • Samuel Adams Brewery (4.8 mi / 7.8 km)

Exploring the natural features in Milton

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Milton is a great spot to appreciate mother nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (7.3 mi / 11.7 km)
  • Copley Square (7 mi / 11.2 km)
  • Boston Harbor (7.9 mi / 12.7 km)
  • Wollaston Beach (3.4 mi / 5.5 km)
  • Arnold Arboretum (4.5 mi / 7.2 km)
  • Carson Beach (5.3 mi / 8.5 km)

How to get to and around Milton

The nearest airport is in Norwood, MA (OWD-Norwood Memorial), located 7.2 mi (11.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8 mi (12.8 km) away.

You can see more of Milton by jumping on the metro at Milton Station, Central Ave. Station or Valley Rd. Station.

Frequently asked questions

What is the best area to stay in Milton when booking a holiday rental?
When considering a holiday rental in Milton, Massachusetts, the neighbourhood of East Milton stands out as an excellent choice. This vibrant area is known for its charming atmosphere and convenient access to a variety of local attractions. One can easily explore the picturesque Milton Village, which boasts an array of quaint shops and cafes, great for a leisurely afternoon. Additionally, East Milton is close to the scenic Blue Hills Reservation, a wonderful spot for outdoor enthusiasts offering hiking trails and stunning views.Another appealing option is the area surrounding Milton's historic district, which is characterised by beautiful homes and a rich history. Staying here provides easy access to the Milton Art Museum, where visitors can appreciate local art and culture. The neighbourhood is also well-connected, ensuring that you can easily venture into nearby Boston for further exploration.
What is the most popular type of holiday rental accomodation in Milton?
In Milton, apartments are the most popular type of holiday rental, with around 44 available throughout the area. These apartments are typically located in peaceful neighbourhoods, offering a comfortable and home-like atmosphere. Most units come equipped with fully functional kitchens, spacious living areas, and often a balcony or patio for enjoying the outdoors.For those seeking more space, there are approximately 36 holiday houses available, which are ideal for families or larger groups. These homes generally feature multiple bedrooms, private gardens, and outdoor seating areas, providing ample space for relaxation and socialising.
Are there any family house rentals in Milton?
In Milton, Massachusetts, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. This charming town features lovely neighbourhoods such as Milton Village and East Milton, where visitors can find spacious homes equipped with multiple bedrooms and ample living space for families to relax together. Many of these properties come with amenities like fully equipped kitchens, allowing for easy meal preparations, and cosy backyards for outdoor play.Additionally, the locale is conveniently located near parks such as the picturesque Milton Cemetery and the expansive Blue Hills Reservation, offering opportunities for hiking, picnicking, and enjoying nature. The area's proximity to Boston also means that families can easily explore the city's cultural attractions, museums, and entertainment options.
Are there pet-friendly house rentals in Milton?
In Milton, there are several pet-friendly house rentals available, providing a welcoming environment for both travellers and their furry companions. Many of these holiday homes come equipped with modern amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces that are ideal for pets to enjoy.The neighbourhood itself offers a mix of suburban charm and proximity to nature, with parks like Milton Cemetery and the scenic Blue Hills Reservation nearby, which features hiking trails and open spaces superb for walks with pets.
Are there any remote work holiday rentals in Milton?
In Milton, Massachusetts, there are a variety of remote work holiday rentals available, with approximately 64 options to choose from. Many properties cater to the needs of remote workers, featuring dedicated workspaces equipped with desk chairs and high-speed internet access. This allows for a comfortable and productive environment for those working remotely.The area itself offers a pleasant suburban atmosphere, with convenient access to local amenities. Nearby, you can explore parks and recreational areas, great for taking breaks or enjoying outdoor activities. Additionally, the proximity to Boston provides easy access to a range of cultural attractions and dining options, making it an ideal location for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Milton?
In Milton, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals. Many properties also offer onsite parking for convenience, making it easier for travellers with vehicles. Additionally, rentals often feature coffee and tea makers, superb for starting the day with a warm beverage. For those seeking comfort, fireplaces are a common amenity, adding a cosy touch to the stay. Moreover, some rentals are pet-friendly, suiting travellers who wish to bring their furry companions along.
When is the best time to visit Milton for a holiday rental?
The best time to visit Milton for a holiday rental is during the vibrant summer months, particularly July. This period marks the peak season from July to September, when the weather is pleasantly warm, and outdoor activities abound. With temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for hiking, picnicking, and exploring the beautiful parks and natural spaces that Milton has to offer.July is especially popular, as visitors flock to enjoy community events and local festivals, creating a lively option throughout the town. The extended daylight hours provide ample time for sightseeing and enjoying the area's rich history, including its charming historic architecture and scenic landscapes.For those considering a visit to Milton on a budget, December offers a quieter and more affordable option. It's cooler, with temperatures dipping to around 0 degrees Celsius, you can still appreciate the serene beauty of the town during the winter months, along with festive holiday decorations.
What are the top attractions in Milton?
In Milton, visitors can explore a variety of attractions that showcase the town's natural beauty and historical significance. The Blue Hills Reservation is a standout feature, offering numerous hiking trails, scenic vistas, and opportunities for outdoor activities such as biking and picnicking. This expansive area provides a great escape for nature enthusiasts.Additionally, the famous Milton Academy, a prestigious preparatory school, boasts beautiful grounds and historic buildings that are of interest to those who appreciate architecture and education. The nearby Wollaston Golf Club offers a lovely setting for golf aficionados, while the quaint Milton Village is home to charming shops and local eateries that reflect the community's character.For families, the Tucker Street Park provides a welcoming space for children to play, making it a great spot for a leisurely afternoon.
Are all fees included in the Milton holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Milton holiday homes with parking?
Stayz offers a wide selection of holiday homes in Milton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Milton holiday homes?
You can find great discounts on holiday homes in Milton on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Milton holiday home booking on Stayz?
To find Milton holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Milton?
A long-stay holiday home in Milton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Milton holiday home?
Book your Milton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Milton?
Prices for holiday homes in Milton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Milton to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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