Photo by David Cedrone

Dorchester vacation rentals

We found 1,299 vacation rentals — enter your dates for availability

Discover a selection of 33 homes, 71 apartments, and other vacation rentals in Dorchester that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, which might include parking and a garden. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Dorchester

Showing deals for:Nov 14 - Nov 21
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Find out more about Dorchester

Find out more about Dorchester

Why visit Dorchester

  1. Cultural richness: Dorchester offers a vibrant blend of local culture, making it perfect for family vacations.
  2. Beautiful parks: Enjoy the serenity of urban parks like Dorchester Park, ideal for relaxation and outdoor activities.
  3. Historic charm: Explore the area's rich history, with nearby historic colleges and universities enhancing your visit.
  4. Welcoming atmosphere: Friendly locals and urban vibes create a unique and inviting travel experience.
  5. Diverse accommodations: Choose from a variety of vacation rentals, ensuring a comfortable stay tailored to your needs.

Popular types of accommodation around Dorchester

Planning a getaway to Dorchester? Discover the charm of this vibrant area with a range of vacation rentals tailored to your needs. From inviting houses and cozy apartments to stylish condominiums, Dorchester offers diverse options for every traveller. Whether you're seeking a home away from home or a convenient base for exploration, you'll find the perfect holiday rental to make your stay memorable.

  • Houses: The top choice for visitors to Dorchester, these homes offer spacious and comfortable accommodations for families or groups.
  • Apartments: A popular option for those seeking a central location, apartments provide a home-like atmosphere with convenient amenities.
  • Condos: These modern dwellings combine luxury and comfort, making them an excellent choice for a stylish stay.
  • Cottages: Quaint and charming, cottages offer a peaceful retreat for a relaxing getaway.
  • House Boats: A unique lodging experience, house boats allow you to enjoy the water while staying in Dorchester.**

Top attractions around Dorchester

Dorchester, a vibrant neighbourhood in Boston, is perfect for culture-themed family vacations and urban adventures. Visitors can explore urban parks, historic colleges and universities, and event venues, making it ideal for travellers seeking cultural, city, and outdoor experiences. Whether you're travelling solo, with family, or friends, Dorchester offers a delightful mix of attractions to enrich your trip.

  1. Fenway Park: A historic sports stadium, Fenway Park offers a unique atmosphere filled with rich baseball history and culture. Experience the excitement of a game or take a guided tour to learn about its legendary past, all while soaking in the vibrant sports vibes.
  2. TD Garden: This dynamic event venue hosts a variety of events, from concerts to sporting matches. Immerse yourself in the bustling business vibes and enjoy the electric atmosphere that makes every event memorable.
  3. Boston Common: As the oldest city park in the U.S., Boston Common provides a serene escape with its lush greenery and family-friendly activities. Enjoy outdoor leisure, picnics, or a leisurely stroll in the heart of the city.

Things to do recommended for couples

For a romantic getaway in Dorchester, enjoy a concert at the House of Blues, just 4.8km away, or immerse yourselves in dance at the Roxbury Center for Arts, only 1.6km away. For adventure, consider sailing at the Courageous Sailing Center, located 8.0km from Dorchester.

Things to do recommended for families

During your family vacation in Dorchester, explore the lively Agganis Arena for sports excitement, visit the Charles Hayden Planetarium for engaging entertainment, and unwind at Larz Anderson Park, perfect for relaxation and wellness activities suitable for all ages.

Things to do recommended for groups

Explore the vibrant Faneuil Hall Marketplace for shopping and entertainment, catch a show at the Charles Playhouse for a cultural experience, and indulge in a tour at the Samuel Adams Brewery for a taste of local craft beer, all within a short distance from Dorchester.

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

If you’re planning a trip with a group, family, or pets, or if you’re considering extended stays, be sure to use the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Dorchester with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Dorchester with young kids: Traveling with little ones can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Dorchester: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Dorchester: If you're in search of vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Dorchester

Exploring Dorchester, Boston, offers a vibrant blend of culture and family-friendly experiences. Nestled between Dorchester Avenue and the town centre, you'll find beautiful parks, rich history, and a welcoming atmosphere. Discover the charm of the Dorchester neighbourhood, where friendly locals and urban vibes create a unique travel experience. Whether you're enjoying the serenity of Dorchester Park or delving into local culture, this area promises memorable adventures for every type of traveller.

  • Downtown Boston: Located approximately 6.4km from Dorchester, Downtown Boston is the bustling core of the city, where visitors can immerse themselves in a rich tapestry of culture and history. This vibrant area is famous for its shopping malls and centres, making it a perfect destination for retail therapy. Iconic landmarks like historic sports stadiums and event conference venues add to the allure. Downtown Boston is also an excellent spot for family outings, offering various educational experiences and attractions that cater to all ages.
  • Meeting House Hill: Just 322m from Dorchester, Meeting House Hill is a charming neighbourhood that embodies the spirit of Boston’s local culture. It’s an inviting area for families and cultural enthusiasts alike, with easy access to educational institutions and shopping centres. The neighbourhood is home to historic college universities and sports stadiums, offering a unique blend of academic and athletic experiences. Meeting House Hill’s close-knit community vibe and local attractions make it a delightful stop on your Boston adventure.
  • Fields Corner West: Located a mere 483m away from Dorchester, Fields Corner West is a dynamic neighbourhood that appeals to families, business travellers, and city explorers. This area boasts a variety of shopping options, including centres and malls, alongside educational opportunities. Visitors can enjoy the urban park and historic sites nearby, providing a perfect blend of leisure and learning. Fields Corner West is an excellent choice for those seeking a taste of local life, with its diverse offerings and welcoming atmosphere.

Best time to go to Dorchester

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverageSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnySlightly HighAverage
October55.6°F (13.1°C)Light RainMostly SunnySlightly LowAverage
November44.4°F (6.9°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for an extended stay. To find a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new trips, keep your travel arrangements on track, and manage your bookings efficiently. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Dorchester?
In Dorchester, apartments are the most popular type of vacation rental, with around 61 available throughout the neighbourhood. These apartments are typically situated in vibrant areas, providing easy access to local attractions and amenities. Most feature fully equipped kitchens, comfortable living areas, and often include a balcony or terrace for enjoying the outdoors.
Are there any beach house rentals in Dorchester?
In Dorchester, Massachusetts, there are approximately 42 beach house vacation rentals available, primarily located near the picturesque coastline and close to popular attractions such as the scenic Malibu Beach and the vibrant Savin Hill. These beach houses typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor decks or patios ideal for enjoying the sea breeze. Many properties offer multiple bedrooms, making them suitable for families or larger groups seeking a comfortable retreat by the beach.
How much does it cost to rent a vacation home in Dorchester?
Prices for vacation rentals in Dorchester 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. Vrbo offers something for every taste and budget, from affordable rentals in Dorchester to more spacious homes.
Are there any discounts for Dorchester vacation house rentals?
You can find great discounts on house rentals in Dorchester 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.
Are there any Dorchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Dorchester 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.
Can I find long-stay vacation rentals in Dorchester?
A long-stay vacation rental in Dorchester 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 Dorchester for a vacation rental?
July is the most popular time to visit Dorchester, Massachusetts, as it falls within the peak season that runs from July to September. During this vibrant summer month, travellers flock to the area to enjoy the warm weather and participate in outdoor activities, including exploring the beautiful parks and waterfront areas. The average temperature in July hovers around the mid to high 20s Celsius, creating great conditions for sightseeing and leisurely strolls along Dorchester's scenic coastline.

For those who appreciate a lively atmosphere, July offers plenty of events and community gatherings, making it an exciting time to immerse yourself in local culture. The summer months are also ideal for enjoying nearby attractions, such as the iconic Boston Harbour, which is just a short distance away.

If you're looking for a more budget-friendly option, consider visiting in October. This month, while quieter, presents a lovely opportunity to experience the beautiful autumn foliage and enjoy pleasant temperatures averaging around 15 to 20 degrees Celsius. October's charm lies in its serene environment, allowing for peaceful walks and appreciation of the historic architecture without the summer crowds.
Are there any remote work vacation rentals in Dorchester?
In Dorchester, Massachusetts, there are numerous remote work vacation rentals available, with around 91 options to choose from. This vibrant neighbourhood offers a blend of urban convenience and local charm, making it an excellent choice for those looking to balance work and leisure. Many of the properties are well-equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, desk chairs, and even computer monitors in some cases. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Dorchester vacation rental?
Book your Dorchester vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Dorchester?
In Dorchester, Massachusetts, visitors can explore an array of attractions that reflect the area's rich history and vibrant culture. The John F. Kennedy Presidential Library and Museum, located along the waterfront, offers insights into the life and legacy of the 35th President, set against a backdrop of stunning views of Boston Harbour. Just a short distance away, the Franklin Park Zoo provides a family-friendly environment with diverse animal exhibits and beautiful gardens, making it a great spot for a day out.
Can I change or cancel my Dorchester home rental booking on Vrbo?
To find Dorchester vacation 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 Dorchester vacation 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.

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