Dorchester holiday lettings

We found 1,374 holiday rentals — enter your dates for availability

Discover a selection of 34 homes, 74 apartments and other holiday rentals in Dorchester that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden 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 - Dorchester

Showing deals for:13 Mar - 20 Mar

Image gallery for Sunlit Spacious 3BR in Heart of Downtown Boston! Guest Favorite!

Living Room
10 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)

Sunlit Spacious 3BR in Heart of Downtown Boston! Guest Favorite!

Boston, MA

8% off
Price is £4,251
for 7 nights, 1 apartment
£607 per night
includes taxes & fees
Sunlit Spacious 3BR in Heart of Downtown Boston! Guest Favorite!

Find spaces that suit your style

Why visit Dorchester

  • Cultural richness: Explore Dorchester's vibrant heritage through its historic colleges, universities, and diverse cultural events.
  • Urban parks: Enjoy outdoor adventures in beautiful parks, perfect for family picnics and leisurely strolls.
  • Stunning coastal views: Visit nearby Weymouth Beach for breathtaking sea views and relaxation by the shore.
  • Welcoming community: Experience the friendly locals and warm atmosphere that make Dorchester feel like home.
  • Variety of accommodations: Choose from charming holiday homes, stylish apartments, or modern condos for a perfect stay.

Popular types of accommodation around Dorchester

If you're contemplating a getaway to Dorchester, you're in for a treat! This charming town offers a variety of popular vacation rentals, including private holiday homes, cosy apartments, and modern condos. Whether you’re searching for spacious house rentals, stylish apartments with multiple bedrooms, or inviting guest houses, you'll find the perfect base for your stay. Let us help you discover the ideal accommodation to make your Dorchester experience unforgettable.

  • Houses: The most sought-after option in Dorchester, offering spacious and comfortable settings for families or groups.
  • Apartments: A popular choice for couples or solo travellers, providing convenient access to local amenities.
  • Condos: A great alternative for those looking for a blend of community living and private space.
  • Cottages: Ideal for a quaint retreat, these charming dwellings offer a cosy escape.
  • House Boats: A unique lodging experience, perfect for those wanting to stay on the water.**

Top attractions near Dorchester

Dorchester offers a delightful blend of cultural, family-friendly, and city-themed experiences perfect for any traveller. Explore the urban parks, historic colleges and universities, and vibrant event venues that showcase the area's rich heritage. Whether you're seeking outdoor adventures or cultural insights, Dorchester provides a variety of attractions to make your visit memorable.

  • Fenway Park: A historic sports stadium steeped in baseball culture, Fenway Park offers an electric atmosphere for sports enthusiasts. Just 1.9km from Dorchester, you can immerse yourself in the tradition of America's pastime while enjoying the vibrant local spirit.
  • TD Garden: Located 2.5km from Dorchester, TD Garden serves as a premier venue for major events and conferences. With its dynamic business vibes, it’s a hub for entertainment and sports, making it a must-visit for any visitor to Boston.
  • Boston Common: This expansive urban park, situated 2.5km from Dorchester, is perfect for families and outdoor lovers. Boston Common offers beautifully landscaped areas, walking paths, and a lively city atmosphere, ideal for a relaxing day out.

Things to do recommended for couples

For a romantic getaway in Dorchester, explore the vibrant House of Blues just 1.9km away for live music, or enjoy the cultural charm at the Roxbury Center for Arts, a mere mile from your stay. Don't miss the exhilarating Blue Hills Ski Area, 3.7km away, for some fun on the slopes.

Things to do recommended for families

Families visiting Dorchester can experience the excitement of Agganis Arena, enjoy the serene atmosphere at Larz Anderson Park, and explore the captivating Charles Hayden Planetarium, all within a short distance. These attractions offer a delightful mix of sports, relaxation, and entertainment for a memorable day out.

Things to do recommended for groups

Explore Faneuil Hall Marketplace for a vibrant shopping experience, visit the Samuel Adams Brewery for a taste of local brews, and enjoy a show at the Wilbur Theatre, all within a short distance from Dorchester. These activities promise entertainment and memorable moments for your group.

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

If you're travelling with a group, as a family, with your pets, or seeking extended stays, it's important to apply the right filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Dorchester with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Dorchester with young kids: Journeying with young children can present its difficulties. It's essential to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Dorchester: For many families, a holiday isn't truly fulfilling unless their furry companions are included. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone can feel completely at home.
  • Planning for a long term stay visiting Dorchester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. 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 near Dorchester

Embarking on a holiday in Dorchester, Boston offers an enriching blend of culture and family-friendly experiences. This vibrant neighbourhood allows visitors to explore the historical charm of the area while enjoying the urban atmosphere. Nearby attractions like Weymouth Beach provide stunning sea views and opportunities for relaxation. With friendly locals and a welcoming vibe, Dorchester is the ideal base for discovering the delightful Dorset coast and its picturesque surroundings.

  • Boston: Boston is a vibrant metropolis located a mere 2.5km from Dorchester. This historic city is a cultural hub, attracting visitors with its rich heritage, diverse arts scene, and family-friendly activities. You can explore iconic landmarks such as the Freedom Trail, catch a concert at the renowned TD Garden, or indulge in shopping at the bustling malls. With a plethora of educational institutions and historic sports venues, Boston offers an enriching travel experience that combines city life with a strong sense of history.
  • Downtown Boston: Situated just 2.5km from Dorchester, Downtown Boston is the heart of the city, brimming with energy and excitement. This neighbourhood is ideal for those seeking a blend of culture and family-oriented experiences. Stroll through the vibrant streets filled with shops, dine at chic restaurants, or visit historic sites like the Boston Common. With easy access to major event venues and sports stadiums, Downtown Boston provides a lively atmosphere perfect for both leisure and entertainment.
  • Meeting House Hill: Meeting House Hill is a charming neighbourhood located only 124m away from Dorchester. This area offers a unique cultural experience with its historic charm and community feel. Visitors can enjoy local shopping centres and educational facilities, making it a great spot for families. The proximity to historic colleges and sports venues adds to its appeal, allowing for leisurely exploration and a taste of local life. Meeting House Hill is perfect for those wanting to experience a friendly, residential vibe while still being close to the city's attractions.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageAverage
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 LowSlightly High
November44.4°F (6.9°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next holiday? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo accommodation that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new getaways, pick up where you last paused, or review and organise your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To make the most of 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 Dorchester?
In Dorchester, apartments are the most popular type of holiday rental, with around 61 available throughout the neighbourhood. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and in many cases, access to shared facilities like fitness centres or rooftop decks, providing great views of the city.
Are there any beach house rentals in Dorchester?
In Dorchester, Massachusetts, there are approximately 42 beach house holiday rentals available, primarily scattered along the scenic coastline. These properties range from charming cottages to spacious family homes, all providing a comfortable and inclusive setting. Most beach houses come equipped with modern amenities, including fully furnished kitchens, open living areas, and outdoor decks or patios, great for enjoying the ocean breeze and stunning views. Many of these rentals are located near popular spots such as Dorchester Bay and the picturesque beaches of Savin Hill, making them ideal for both relaxation and exploration.
How much does it cost to rent a holiday home in Dorchester?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Dorchester holiday 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 holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday rentals in Dorchester?
A long-stay holiday 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 holiday rental?
July is the most popular time to visit Dorchester, Massachusetts, making it an exciting choice for those seeking vibrant summer experiences. During this peak season, from July to September, the area buzzes with activity, offering a wealth of outdoor adventures, cultural events, and a lively atmosphere. Visitors can enjoy warm temperatures, often reaching the mid-20s Celsius, superb for exploring parks, beaches, and local attractions.

In Dorchester, July stands out with a host of events, including summer festivals and outdoor concerts, providing ample opportunities to soak up the local culture and mingle with fellow travellers. The pleasant weather encourages leisurely strolls along the waterfront and visits to nearby historical sites.

For those looking to enjoy Dorchester while being mindful of their budget, October presents a wonderful alternative. This month features cooler temperatures, typically in the low teens Celsius, and a quieter atmosphere, allowing for peaceful walks through scenic parks and parks adorned with autumn colours.
Are there any remote work holiday rentals in Dorchester?
In Dorchester, Massachusetts, there are numerous remote work-friendly holiday rentals available, with around 91 options to choose from. This vibrant neighbourhood is well-suited for those looking to balance work and leisure, with many properties offering essential amenities for remote work, such as reliable Wi-Fi, dedicated desk spaces, and comfortable office chairs. Some rentals also feature additional conveniences like computer monitors and safes, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Dorchester holiday rental?
Book your Dorchester 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 Dorchester?
In Dorchester, Massachusetts, visitors can explore a variety of attractions that showcase the area's rich history and vibrant culture. The Franklin Park Zoo, located within Franklin Park, offers a delightful experience for families and animal lovers alike, featuring a diverse range of wildlife and beautiful walking paths. Nearby, the John F. Kennedy Presidential Library and Museum provides insights into the life and legacy of the former president, set against a stunning backdrop of Boston Harbour.
Can I change or cancel my Dorchester home rental booking on Vrbo?
To find Dorchester 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Dorchester 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas