Dorchester holiday homes

We found 1,456 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:1 Jan - 8 Jan

Interior
Private kitchen
Dining
Exceptional
(98 reviews)

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

Boston

8% off
NZ$15,664
for 7 nights, 1 home
NZ$2,238 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Living area
Private kitchen
Private kitchen
Room
Exceptional
(32 reviews)

Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH

Boston

8% off
NZ$8,561
for 7 nights, 1 apartment
NZ$1,223 per night
includes taxes & fees
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Interior
Living area
Room
Interior
Exceptional
(21 reviews)

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

Boston

8% off
NZ$6,393
for 7 nights, 1 home
NZ$913 per night
includes taxes & fees
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

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

Boston

20% off
NZ$11,345
for 7 nights, 1 home
NZ$1,621 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Dining
Private kitchen
Living area
Interior
Wonderful
(24 reviews)

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

Boston

8% off
NZ$6,462
for 7 nights, 1 apartment
NZ$923 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Interior
Interior
Room
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
NZ$7,491
for 7 nights, 1 home
NZ$1,070 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Dining
Interior
Private kitchen
Room
Excellent
(7 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
NZ$8,838
for 7 nights, 1 apartment
NZ$1,263 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Interior
Living area
Interior
Private kitchen
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
NZ$7,377
for 7 nights, 1 apartment
NZ$1,054 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Exterior detail
Living area
Dining
Exterior detail
Very good
(19 reviews)

Pet-Friendly 3BR 2BA Boston 1st-floor Apt • Franklin Park & Red Line 5581

Boston

8% off
NZ$5,496
for 7 nights, 1 apartment
NZ$785 per night
includes taxes & fees
Pet-Friendly 3BR 2BA Boston 1st-floor Apt • Franklin Park & Red Line 5581
Bedroom 2,
Cool Historic Details in this 1860's townhome apartment,  stairs required!
Roof top deck with city views!!
Dining
Exceptional
(47 reviews)

Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!

Boston

8% off
NZ$8,688
for 7 nights, 1 apartment
NZ$1,241 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Living area
Dining
Room
Living area
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
NZ$6,420
for 7 nights, 1 apartment
NZ$917 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Interior
Interior
Room
Private kitchen
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
NZ$7,116
for 7 nights, 1 apartment
NZ$1,017 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Welcome!
Dining
Great Room with 12 foot ceilings and large windows.
Interior
Exceptional
(37 reviews)

**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!

Boston

8% off
NZ$8,720
for 7 nights, 1 apartment
NZ$1,246 per night
includes taxes & fees
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Interior
Private kitchen
Dining
Private kitchen
Exceptional
(35 reviews)

988-Cozy, Lovely and Renovated 4BR-2BA apartment in Boston

Boston

8% off
NZ$6,305
for 7 nights, 1 apartment
NZ$901 per night
includes taxes & fees
988-Cozy, Lovely and Renovated 4BR-2BA apartment in Boston
Located on floor 2 of a classic Boston 1860's Rowhouse
Living area
Open Kitchen/Dining Area
Entrance/steps to apartment. Please note,  steps required
Exceptional
(90 reviews)

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

Boston

8% off
NZ$2,822
for 7 nights, 1 apartment
NZ$403 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Interior
Interior
Interior
Room
Exceptional
(18 reviews)

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

Boston

8% off
NZ$8,881
for 7 nights, 1 home
NZ$1,269 per night
includes taxes & fees
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Terrace/patio
Room
Living area
Private kitchen
Exceptional
(26 reviews)

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

Cambridge

15% off
NZ$5,432
for 7 nights, 1 home
NZ$776 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
A six-seat dining table makes it perfect for meals together!
Room
The living room is thoughtfully designed, offering a warm & inviting atmosphere.
With stylish touches, cozy seating, and plenty of room to unwind
Exceptional
(5 reviews)

Family-Friendly 3BR Apartment Close to Everything

Boston

8% off
NZ$5,296
for 7 nights, 1 apartment
NZ$757 per night
includes taxes & fees
Family-Friendly 3BR Apartment Close to Everything
Interior
Living area
Room
Property grounds
Wonderful
(9 reviews)

90- SPRING GETAWAY EARLY BIRD 10% OFF! Boston spacious 4BR apartment with view

Boston

8% off
NZ$6,166
for 7 nights, 1 apartment
NZ$881 per night
includes taxes & fees
90- SPRING GETAWAY EARLY BIRD 10% OFF! Boston spacious 4BR apartment with view
Open Space with Doors available for privacy between Kitchen/ Bedroom
Isabella Stewart Gardner Museum, Walking distance from Inn
Fort Hill Inn,  Boston.   Main Building  forthillinn.com
Modern with nice Historic Details,  Original Decorative Marble Fireplace
Exceptional
(83 reviews)

Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center

Boston

8% off
NZ$2,822
for 7 nights, 1 apartment
NZ$403 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Interior
Private kitchen
Exterior detail
Dining
Exceptional
(28 reviews)

New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602

Boston

8% off
NZ$5,511
for 7 nights, 1 apartment
NZ$787 per night
includes taxes & fees
New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602
Interior
Interior
Exterior
Private kitchen
Wonderful
(18 reviews)

Spacious 4BR Boston 1st-floor Apt w/ Free parking • Pet-friendly 301

Boston

8% off
NZ$4,343
for 7 nights, 1 apartment
NZ$620 per night
includes taxes & fees
Spacious 4BR Boston 1st-floor Apt w/ Free parking • Pet-friendly 301
Dining
Exterior detail
Living area
Open Kitchen
Wonderful
(6 reviews)

Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center

Boston

8% off
NZ$4,876
for 7 nights, 1 apartment
NZ$697 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Interior
Private kitchen
Dining
Living area
Wonderful
(6 reviews)

74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy

Quincy

8% off
NZ$3,699
for 7 nights, 1 apartment
NZ$528 per night
includes taxes & fees
74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy
  • Peace of mind

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  • All the privacy of home

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

    More space, more privacy, more amenities — more value

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.0°F (-1.1°C)Light RainMostly SunnyAverage
February31.5°F (-0.3°C)Light RainMostly CloudyAverage
March37.9°F (3.3°C)Light RainMostly SunnyAverage
April48.2°F (9.0°C)Light RainMostly SunnyAverage
May58.5°F (14.7°C)Light RainMostly SunnySlightly Low
June66.6°F (19.2°C)Light RainMostly SunnyAverage
July73.6°F (23.1°C)Light RainMostly SunnySlightly High
August72.7°F (22.6°C)Light RainMostly SunnySlightly High
September65.7°F (18.7°C)Light RainMostly SunnySlightly High
October55.6°F (13.1°C)Light RainMostly SunnySlightly Low
November44.4°F (6.9°C)Light RainMostly SunnyAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly 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. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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