We found 1,457 holiday rentals — enter your dates for availability
Discover a selection of 35 homes, 70 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:12 Feb - 19 Feb
Image gallery for Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
1010 out of 10, Exceptional, (103 reviews)
Exceptional
(103 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Good location, well appointed and very clean rooms. Pricier rooms generously sized, cheaper rooms quite small. Good to have a microwave. Not having any staff onsite (apart from cleaners) isn’t ideal when you need some help, advice or recommendations. Generally messages would be responded to, but not always straight away. When changing from one room to another I was initially given the wrong door code and it took several hours to resolve - it was eventually resolved (thank you!) but would have been so sooner if someone was there.
Everything was great. Washer/Dryer was handy. Close to everything. Wish there were oven trays as we bought pizza and chips to make back at the apartment.
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Find out more about Dorchester
Why visit Dorchester
Cultural richness: Dorchester boasts a vibrant arts scene and historical landmarks that reflect its diverse heritage.
Urban parks: Enjoy the beautiful green spaces, perfect for family outings and outdoor activities.
Local history: Explore the Dorchester Antiquarian for a glimpse into the area's unique past.
Friendly community: Experience the warm hospitality of locals in the charming streets of Dorchester Centre.
Family-friendly activities: Discover numerous attractions that cater to all ages, making it an ideal family destination.
Top attractions in and around Dorchester
Dorchester, a vibrant neighbourhood in Boston, is ideal for family and culture-themed holidays. Visitors can explore urban parks, charming streets, and historic churches, offering a rich urban experience. Don’t miss the chance to visit the Dorchester Antiquarian for a taste of local history and culture. This diverse area provides a perfect blend of outdoor adventures and cultural insights, making it a delightful destination for travellers seeking to immerse themselves in the heart of Boston.
John F. Kennedy Presidential Library and Museum: Immerse yourself in rich history and vibrant culture at this captivating museum, nestled within Dorchester, showcasing artefacts and stories from a pivotal era.
Newbury Street: Enjoy a short jaunt from Dorchester to this bustling street, where city energy meets delightful shops and cafes.
The Freedom Trail: Experience the spirit of American history on this notable trail, offering a cultural journey through historical landmarks.
Things to do recommended for couples
Looking for a romantic getaway in Dorchester? Enjoy a leisurely stroll along the scenic Neponset River, explore the charming local cafés, or share a picnic at Franklin Park. Don't miss the stunning sunset views from the shore; it’s the perfect backdrop for a memorable evening together.
Things to do recommended for families
Families visiting Dorchester can explore the Boston Museum of Science with its hands-on exhibits, enjoy a day at Franklin Park Zoo to see diverse wildlife, and relax at Pope John Paul II Park for outdoor fun and picnics. It's a fantastic destination for kids and parents alike.
Things to do recommended for groups
Groups visiting Dorchester can enjoy a vibrant cultural experience at the Strand Theatre, explore the historic Franklin Park Zoo, and indulge in local cuisine at the diverse eateries along Dorchester Avenue. Don't miss a leisurely stroll through the scenic parks for a taste of the area's natural beauty.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
What do I need to keep in mind when booking a vacation around Dorchester
Whether you’re travelling with a group, as a family, with your pets, or seeking extended stays, ensure you filter by the appropriate priorities. Here are some Vrbo booking tips for you.
Traveling to Dorchester with a group: Consider how many bedrooms you'll require and think about additional features like a fully-equipped kitchen or an outdoor area for group get-togethers. Luckily, you can filter for all these options and more on Vrbo.
Traveling to Dorchester with young kids: Traveling with little ones can be a challenge. You need to ensure they’re comfortable and safe, with age-appropriate facilities like a private swimming pool. It’s also wise to consider how close you are to attractions that are friendly for the whole family.
Taking your pets with you to Dorchester: For many, a family holiday isn’t complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels right at home.
Planning for a long term stay visiting Dorchester: If you’re after holiday rentals with special offers for month-long stays, you’ve come to the right spot. Use the appropriate filter to quickly find and save on monthly accommodations. You might also want to include extras like a parking space, a well-equipped kitchen, or your very own private pool in your search.
Where to stay near Dorchester
Dorchester, a vibrant neighbourhood in Boston, offers a rich tapestry of culture and history. Visitors can explore its diverse parks, enjoy family-friendly activities, and immerse themselves in the local arts scene. The area boasts historical landmarks and a welcoming atmosphere, making it ideal for families and culture enthusiasts alike. Strolling through Dorchester Centre, you’ll experience the warmth of friendly locals and the urban charm of this dynamic neighbourhood.
Boston: As a vibrant metropolis, Boston is a cultural hub that offers a diverse array of experiences. Located in the heart of the city, Dorchester serves as a gateway to explore Boston's rich history and contemporary attractions. Visitors can immerse themselves in educational experiences at renowned institutions, enjoy live music concerts, or indulge in shopping at bustling malls. The city is home to iconic landmarks, including historic sports stadiums and event venues that host a variety of conferences and sports events, making it a destination for families and culture enthusiasts alike.
Back Bay: Situated 5km from Dorchester, Back Bay is a charming neighbourhood known for its stunning Victorian brownstones and vibrant shopping scene. This area is ideal for families and culture seekers, offering easy access to educational institutions and a variety of shopping centres. Visitors can stroll through picturesque urban parks, admire the architecture of historic colleges, and explore local boutiques. Back Bay’s inviting atmosphere and array of attractions make it an excellent choice for those looking to enjoy the essence of Boston.
Seaport District: Located 5km from Dorchester, the Seaport District is a bustling neighbourhood that blends business with leisure. This area is perfect for families and those seeking a city-themed experience. Visitors can explore a range of shopping malls and centres, unwind at local spas, and enjoy waterfront views at the marina. The Seaport is also home to significant venues for events and conventions, making it a dynamic area that caters to both tourists and business travellers, ensuring there’s something for everyone.
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.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
30.0°F (-1.1°C)
Light Rain
Mostly Sunny
Average
February
31.5°F (-0.3°C)
Light Rain
Mostly Cloudy
Average
March
37.9°F (3.3°C)
Light Rain
Mostly Sunny
Average
April
48.2°F (9.0°C)
Light Rain
Mostly Sunny
Average
May
58.5°F (14.7°C)
Light Rain
Mostly Sunny
Slightly Low
June
66.6°F (19.2°C)
Light Rain
Mostly Sunny
Average
July
73.6°F (23.1°C)
Light Rain
Mostly Sunny
Slightly High
August
72.7°F (22.6°C)
Light Rain
Mostly Sunny
Slightly High
September
65.7°F (18.7°C)
Light Rain
Mostly Sunny
Slightly High
October
55.6°F (13.1°C)
Light Rain
Mostly Sunny
Slightly Low
November
44.4°F (6.9°C)
Light Rain
Mostly Sunny
Average
December
36.3°F (2.4°C)
Light Rain
Mostly Sunny
Slightly Low
Booking with Vrbo is simple
Are you aiming to save on your next adventure? One effective way to do so is by being flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property 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 Trip Board provides a convenient way to plan your next adventure, manage your travel arrangements, or review your bookings. Your saved or booked properties are neatly organised into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/trips.
**Based on Vrbo properties bookings.
Frequently Asked Questions
When is the best time to visit Dorchester for a holiday rental?
July is the most popular time to visit Dorchester, Massachusetts, as it marks the beginning of the peak season that runs from July to September. During this vibrant summer period, visitors flock to the area to enjoy the warm weather and partake in various outdoor activities, including exploring the scenic parks and waterfront spaces that Dorchester is known for.
Temperatures in July typically hover around 25 to 30 degrees Celsius, providing an ideal climate for sightseeing and enjoying the beautiful landscapes. This is particularly appealing for families and adventure seekers who appreciate the convenience of being close to Boston's cultural attractions while still enjoying the relaxed atmosphere of Dorchester.
For those looking for a more cost-effective holiday, October is a wonderful option. This month offers a quieter experience, allowing you to explore the charming neighbourhoods and local eateries at a leisurely pace while enjoying the crisp autumn air and stunning fall foliage.
Ultimately, the best time to book a holiday rental in Dorchester depends on your preferences. If you thrive in a lively option filled with summer activities, July will be your superb choice. Conversely, if you prefer a tranquil escape with beautiful autumn scenery, October provides a fantastic alternative.
What are the top attractions in Dorchester, Massachusetts, United States of America?
In Dorchester, visitors can explore a variety of attractions that highlight the area's rich history and cultural diversity. The John F. Kennedy Presidential Library and Museum, located on the waterfront, offers insights into the life and legacy of the 35th President of the United States. Nearby, the scenic Boston Harborwalk provides a lovely space for walking and enjoying views of the water.
Another significant site is the Dorchester Historical Society, where guests can learn about the local history through various exhibits and preserved buildings. For those interested in green spaces, Franklin Park, part of the Emerald Necklace park system, features walking trails, a zoo, and recreational areas, making it a superb spot for outdoor activities.
Are all fees included in the Dorchester holiday homes prices shown on Bookabach?
Bookabach 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 Dorchester holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 Dorchester holiday homes?
You can find great discounts on holiday homes in Dorchester on Bookabach, 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 Dorchester holiday home booking on Bookabach?
To find Dorchester holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Dorchester?
A long-stay holiday home 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 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 Bookabach?
Bookabach'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 Dorchester holiday home?
Book your Dorchester 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Dorchester?
Prices for holiday homes 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. Bookabach offers something for every taste and budget, from affordable homes in Dorchester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way.
Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive.
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