Downtown Crossing holiday lettings

We found 418 holiday rentals — enter your dates for availability

Discover a selection of 24 apartments and other holiday rentals in Downtown Crossing that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Downtown Crossing

Showing deals for:30 Jan - 6 Feb
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Downtown Crossing

  • Bustling shopping district: Experience a vibrant mix of historic architecture and modern boutiques, perfect for retail therapy.
  • Cultural experiences: Immerse yourself in Boston's rich history with nearby attractions and urban parks.
  • Scenic strolls: Enjoy leisurely walks through Boston Common and the beautiful urban landscape.
  • Diverse accommodation: Choose from a range of options, including stylish apartments and modern condos with excellent amenities.
  • Local cuisine: Savor delicious food at charming eateries, reflecting the friendly atmosphere of Downtown Crossing.

Popular types of accommodation around Downtown Crossing

Discover a variety of accommodation options in Downtown Crossing with Vrbo, tailored to suit every traveller's needs. Whether you prefer a private vacation home, a stylish apartment, or a modern condo, you'll find excellent amenities, including free parking and stunning views from upper floors. With top hotels nearby, Downtown Crossing is the perfect base for your adventure. Choose the ideal rental for your stay and enjoy the vibrant atmosphere of this bustling area.

  • Houses: The top choice for visitors, these homes offer a unique and comfortable stay, perfect for families or groups seeking a home-away-from-home experience in Downtown Crossing.
  • Apartments: A popular option, apartments provide a convenient and stylish base for exploring the vibrant area, suited for couples or solo travellers.
  • Condos: These modern accommodations offer great amenities and are ideal for those wanting a blend of hotel-like services and home comforts.
  • Cottages: Quaint and charming, cottages are perfect for those seeking a cosy retreat while being close to the city's attractions.
  • House Boats: For a unique experience, house boats offer a distinctive stay on the water, adding a touch of adventure to your trip.**

Top attractions near Downtown Crossing

Downtown Crossing in Boston is perfect for family and culture-themed holidays, offering attractions such as urban parks, historic colleges, and conference venues. Visitors can enjoy a stroll through Boston Common and explore nearby attractions, making it an ideal spot for those seeking a vibrant city experience. With plenty of activities and cultural experiences, Downtown Crossing promises a delightful getaway for tourists of all ages.

  • Fenway Park: A historic sports stadium, Fenway Park is renowned for its rich baseball heritage and vibrant atmosphere, making it a must-visit for sports enthusiasts.
  • TD Garden: This premier event and conference venue is the heartbeat of Boston's sporting and entertainment scene, offering a dynamic mix of live events and business activities.
  • Boston Common: A beautiful urban park, Boston Common invites families and visitors to enjoy its lush greenery, walking paths, and seasonal events in a lively city setting.

Things to do recommended for couples

Looking for a romantic getaway in Boston? Enjoy live music at the House of Blues, embark on an adventure at the Courageous Sailing Center, or immerse yourselves in culture at the Jose Mateo Ballet Theatre. Each offers a unique experience just a stone's throw from Downtown Crossing.

Things to do recommended for families

Families can enjoy the exciting atmosphere at Agganis Arena, just 1.9km from Downtown Crossing, delve into the wonders of the universe at the Charles Hayden Planetarium, only 621m away, or unwind in the serene surroundings of Chestnut Hill Reservation, situated 3.1km from the city centre.

Things to do recommended for groups

Your group can enjoy a vibrant day at Faneuil Hall Marketplace, indulge in culture at Wilbur Theatre, or savour local produce at Boston Public Market, all located within a short walk of Downtown Crossing. These experiences offer a perfect blend of entertainment and local charm.

What do I need to keep in mind when booking a vacation around Downtown Crossing

If you're travelling with a group, family, or pets, or you're seeking longer stays, it's essential to filter your options according to your specific priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Downtown Crossing with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Downtown Crossing with young kids: Journeying with young children can present its difficulties. It's essential to prioritise their comfort and safety, alongside suitable facilities, such as a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Downtown Crossing: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo accommodations that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Downtown Crossing: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly locate and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Downtown Crossing

Downtown Crossing is a vibrant hub in Boston, perfect for families and culture enthusiasts alike. Explore the bustling shopping district, where you’ll find a mix of historic architecture and modern boutiques. The friendly atmosphere invites you to savour the local cuisine and enjoy scenic strolls through this urban landscape. Whether you're indulging in retail therapy or soaking up the rich history, Downtown Crossing promises an unforgettable holiday experience in the heart of Boston.

  • Boston: As a vibrant metropolis located 186m from Downtown Crossing, Boston boasts a rich tapestry of history and culture. Visitors flock to this iconic city for its diverse experiences, from educational institutions to music concerts. The shopping malls and centres here cater to those looking for retail therapy. Key attractions include historic sports stadiums and event venues that resonate with both locals and tourists, making Boston a must-visit for anyone seeking an energetic urban experience.
  • Downtown Boston: Situated a mere 186m from Downtown Crossing, Downtown Boston is a bustling neighbourhood that encapsulates the essence of city life. Ideal for families and culture enthusiasts, it offers a plethora of activities, including educational sites and shopping centres. Notable attractions include historic sports stadiums and event conference venues that enhance the community's vibrant atmosphere. With its blend of family-friendly activities and cultural highlights, Downtown Boston is an essential stop on your journey.
  • Cambridge: Located 1.9km from Downtown Crossing, Cambridge is renowned for its academic heritage and vibrant cultural scene. This city attracts visitors seeking family-friendly experiences, educational opportunities, and a rich cultural landscape. With its historic colleges and universities as key landmarks, Cambridge offers an engaging atmosphere filled with museums, theatres, and charming shops. The proximity to stadiums and historic sports venues adds to its appeal, making Cambridge a delightful destination for those looking to explore beyond the city.

Best time to go to Downtown Crossing

If you're planning a trip to Downtown Crossing, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from February to April, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudySlightly HighSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnySlightly HighSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.6°F (23.1°C)Light RainMostly SunnyAverageSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly SunnySlightly LowAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can result in significant savings. Furthermore, opting for a longer stay often brings about even better deals. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a helpful area for you to plan new journeys, resume your previous arrangements, or keep track of your travel itineraries. You can easily view the properties you’ve saved or booked, neatly organised into categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Downtown Crossing?
In Downtown Crossing, apartments are the most popular type of holiday rental, with around 21 available in this bustling area. These apartments are ideally situated near key attractions such as the Boston Opera House and the historic Downtown Crossing shopping district, offering guests easy access to a variety of dining and entertainment options. Most of these rentals come with amenities like fully equipped kitchens, comfortable living spaces, and some even feature in-unit laundry facilities for added convenience.
How much does it cost to rent a holiday home in Downtown Crossing?
Prices for holiday rentals in Downtown Crossing 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Downtown Crossing to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Downtown Crossing holiday house rentals?
You can find great discounts on house rentals in Downtown Crossing on Vrbo, 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.
What are popular rental amenities in Downtown Crossing?
In Downtown Crossing, popular rental amenities typically include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature a coffee and tea maker, ensuring that visitors can enjoy their morning brews conveniently. For those needing extra sleeping space, sofa beds are commonly available, making these rentals suitable for families or groups. Additionally, some accommodations come with an office area, providing a superb workspace for business travellers or those needing to catch up on tasks while away.
Are there any family house rentals in Downtown Crossing?
In Downtown Crossing, Massachusetts, there are some family-friendly house rentals available, providing a convenient base for exploring the area. This vibrant locale is known for its mix of shopping, dining, and cultural attractions, making it ideal for families. Many of these properties feature spacious living areas, fully equipped kitchens for preparing meals, and comfortable bedrooms that cater to larger groups.
Are there any Downtown Crossing holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Downtown Crossing 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 on Vrbo 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 pet-friendly holiday rentals in Downtown Crossing?
In Downtown Crossing, there are several pet-friendly holiday rentals available, making it a convenient choice for travellers wishing to explore the area with their furry companions. These rentals typically offer modern amenities such as fully equipped kitchens, comfortable living spaces, and Wi-Fi, ensuring a pleasant stay.
Can I find long-stay holiday rentals in Downtown Crossing?
A long-stay holiday rental in Downtown Crossing 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Downtown Crossing for a holiday rental?
February is the most popular time to visit Downtown Crossing, attracting visitors eager to experience the vibrant atmosphere and winter festivities. This period, spanning from February to April, is considered the peak season, with many tourists flocking to enjoy the unique blend of shopping, dining, and cultural events that the area offers.

During these months, you can expect crisp weather, with daytime temperatures typically hovering around 0 to 5 degrees Celsius. While this may be chilly, the season provides a delightful opportunity for outdoor activities and sightseeing, especially with the enchanting backdrop of winter lights and decorations adorning the streets.

For those looking to stretch their travel budget, December presents a more affordable option. This month allows for a quieter experience, great for exploring the local shops and cafés without the hustle and bustle of peak tourist season. Plus, the festive holiday spirit in Downtown Crossing adds a special charm to your visit.
Are there any remote work holiday rentals in Downtown Crossing?
In Downtown Crossing, Massachusetts, there are a variety of remote work holiday rentals available, with around 25 options to choose from. This vibrant area offers a blend of urban energy and convenience, making it an attractive location for those looking to work remotely. Many of the properties feature dedicated workspaces, complete with desks and ergonomic chairs, as well as reliable Wi-Fi to ensure smooth connectivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Downtown Crossing holiday rental?
Book your Downtown Crossing holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Downtown Crossing?
In Downtown Crossing, visitors can immerse themselves in a vibrant mix of shopping, dining, and cultural attractions. The area is home to the historic Boston Opera House, where guests can catch a variety of performances ranging from Broadway shows to concerts. The bustling shopping district features a range of stores, from high-end brands to popular retail chains, making it a great spot for those looking to indulge in some retail therapy.
Can I change or cancel my Downtown Crossing home rental booking on Vrbo?
To find Downtown Crossing holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Downtown Crossing holiday rental prices shown on Vrbo?
Vrbo 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.

More holiday ideas