Dorchester holiday homes

We found 1,524 holiday rentals — enter your dates for availability
Discover a selection of 35 homes, 71 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 Nov - 20 Nov

Interior
Private kitchen
Dining
Exceptional
(90 reviews)

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

Boston

8% off
NZ$21,057
for 7 nights, 1 home
NZ$3,008 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Living area
Private kitchen
Room
Private kitchen
Exceptional
(28 reviews)

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

Boston

8% off
NZ$8,286
for 7 nights, 1 apartment
NZ$1,184 per night
includes taxes & fees
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Room
Interior
Interior
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
NZ$7,250
for 7 nights, 1 home
NZ$1,036 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Dining
Interior
Interior
Room
Very good
(6 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
NZ$8,553
for 7 nights, 1 apartment
NZ$1,222 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Living area
Exterior detail
Interior
Exterior detail
Exceptional
(6 reviews)

3-bedroom 2 baths beautiful victorian with WiFi, AC

Boston

8% off
NZ$7,959
for 7 nights, 1 apartment
NZ$1,137 per night
includes taxes & fees
3-bedroom 2 baths beautiful victorian with WiFi, AC
Living area
Interior
Outdoor private space
Room
Exceptional
(49 reviews)

World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train

Boston

9% off
NZ$6,863
for 7 nights, 1 apartment
NZ$980 per night
includes taxes & fees
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Interior
Living area
Dining
Interior
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
NZ$7,140
for 7 nights, 1 apartment
NZ$1,020 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Dining
Cool Historic Details in this 1860's townhome apartment,  stairs required!
Master Bath Views
Bedroom 2,
Exceptional
(46 reviews)

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

Boston

8% off
NZ$8,408
for 7 nights, 1 apartment
NZ$1,201 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Dining
Spacious 4 BR home for groups. Perfect for relaxing and gathering together
Outdoor dining
Room
Exceptional
(12 reviews)

4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train

Boston

8% off
NZ$7,302
for 7 nights, 1 apartment
NZ$1,043 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Private kitchen
Interior
Room
Interior
Exceptional
(26 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
NZ$6,887
for 7 nights, 1 apartment
NZ$984 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Interior
Dining
Welcome!
Great Room with 12 foot ceilings and large windows.
Exceptional
(37 reviews)

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

Boston

8% off
NZ$8,440
for 7 nights, 1 apartment
NZ$1,206 per night
includes taxes & fees
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Private kitchen
Dining
Living area
Living area
Excellent
(9 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
NZ$6,213
for 7 nights, 1 apartment
NZ$888 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Property grounds
Private kitchen
Living area
Dining
Exceptional
(23 reviews)

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

Boston

8% off
NZ$5,919
for 7 nights, 1 apartment
NZ$846 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Living room, 65" Smart TV, Genuine leather sectional sofa, Book and toys shelf.
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
No.2 Bedroom with a King bed, TV Stand, large screen smart TV and closet
Exceptional
(66 reviews)

Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite

Boston

8% off
NZ$9,199
for 7 nights, 1 apartment
NZ$1,314 per night
includes taxes & fees
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Located on floor 2 of a classic Boston 1860's Rowhouse
Living area
Interior
Open Kitchen/Dining Area
Exceptional
(87 reviews)

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

Boston

8% off
NZ$2,732
for 7 nights, 1 apartment
NZ$390 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Private kitchen
Room
Terrace/patio
Living area
Exceptional
(21 reviews)

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

Cambridge

15% off
NZ$4,461
for 7 nights, 1 home
NZ$637 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Fort Hill Inn,  Boston.   Main Building  forthillinn.com
Isabella Stewart Gardner Museum, Walking distance from Inn
Room
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$2,732
for 7 nights, 1 apartment
NZ$390 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Interior
Exterior detail
Dining
Open Kitchen
Exceptional
(5 reviews)

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

Boston

8% off
NZ$4,719
for 7 nights, 1 apartment
NZ$674 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Fully Open,  bright and airy living Space
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Open City Loft with sleeper sofa
Located on a quiet Private Way,  In The Fort Hill neighborhood.
Exceptional
(85 reviews)

Fresh Modern City Loft Apt! Easy Access to the city!

Boston

8% off
NZ$2,646
for 7 nights, 1 apartment
NZ$378 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!
Room
Living area
Exterior detail
Interior
Exceptional
(18 reviews)

"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center

Boston

8% off
NZ$2,587
for 7 nights, 1 apartment
NZ$370 per night
includes taxes & fees
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Living area
Living area
Private kitchen
Outdoor dining
Exceptional
(39 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
NZ$9,453
for 7 nights, 1 apartment
NZ$1,350 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Interior
Exterior detail
Room
Interior
Exceptional
(39 reviews)

SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston

Boston

8% off
NZ$5,134
for 7 nights, 1 apartment
NZ$733 per night
includes taxes & fees
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
With stylish touches, cozy seating, and plenty of room to unwind
Room
you’ll find all the basics you need for a comfortable stay.
The living room is thoughtfully designed, offering a warm & inviting atmosphere.
Exceptional
(5 reviews)

Family-Friendly 3BR Apartment Close to Everything

Boston

8% off
NZ$5,126
for 7 nights, 1 apartment
NZ$732 per night
includes taxes & fees
Family-Friendly 3BR Apartment Close to Everything
Located on the adjacent Private way.  Outdoor  Deck for guest use.
Interior
Queen Bedroom #2 on Garden Level
Open Dining with Galley Kitchen
Wonderful
(34 reviews)

Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!

Boston

8% off
NZ$4,675
for 7 nights, 1 apartment
NZ$668 per night
includes taxes & fees
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
  • 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, 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

What is the most popular type of holiday home accommodation in Dorchester?
The most sought-after types of holiday homes in Dorchester are apartments. Prefer something different? Bookabach has many options to match our guests' requirements, so you'll see holiday homes in loads of shapes and sizes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday home in Dorchester?
The average price for a holiday home in Dorchester is determined by several factors, including property type, length of stay and time of year. Whether you're thinking about a sprawling villa with space for extended family or a cosy condo perfect for just you and the kids, just enter your travel dates to view stays with terrific value.
How much does it cost to rent a beach house in Dorchester?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Click on your Dorchester travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use the filters to select the features and amenities you need.
Are there pet-friendly holiday homes in Dorchester?
Pack a travel bag and a bone for your puppy dog because Dorchester has 47 holiday homes that put out the welcome mat to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Dorchester?
Add a whole new level of fun to your trip by booking one of the five houses with a private pool in Dorchester. Use our search filter to find properties with pools on Bookabach, then spend carefree days splish-splashing around in a swimming pool that's just for you.
What are popular home amenities in Dorchester?
When it comes to home amenities that guests are looking for in Dorchester, nearby museums, a swimming pool and a nearby waterfront are the most popular. With Bookabach holiday homes, you'll enjoy choices to suit your taste and style, whether you're on a trip with family members, friends or even pets.
Are there large group holiday homes in Dorchester?
With eight properties that can host 10 or more guests in Dorchester, you won't have to cross anyone off the invite list. From extended family holidays to events like Christmas and birthday parties, Bookabach will help you find a large group home that fits the occasion.
Are there holiday homes in Dorchester that welcome kids?
Bring the whole group together for fun-filled adventures in Dorchester at one of our 46 family-friendly holiday homes. These stays come with conveniences that are just perfect for getaways with the little ones, including full kitchens, extra bedrooms and entertainment units. Simply click on the "Properties good for families" filter box and pick out your favourite.
What are the top attractions for families in Dorchester?
Keeping the kids entertained during your stay in Dorchester is simple with these family-friendly attractions:
  • New England Aquarium
  • Museum of Science
  • Boston Tea Party Ship
Are there one-bedroom holiday homes in Dorchester?
You'll find 16 one-bedroom properties in Dorchester to choose from. A one-bedroom holiday home is an excellent option if it's only two of you or if you're travelling on your own. Throw in more convenience, space and privacy compared to a hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday homes in Dorchester?
Dorchester has 11 two-bedroom holiday properties that you can choose from. Book a holiday home with all the comfort and privacy you want at a price that's hard to resist on Bookabach.
Are there holiday homes with WiFi in Dorchester?
Whether you'd like to stay in touch with the news, make a video call or update your social media, there are 13 holiday homes with WiFi in Dorchester. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Dorchester?
Decide on your travel dates and then use the filters to view holiday homes with air conditioning in Dorchester on Bookabach. With 44 air-conditioned properties available here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday home in Dorchester?
The minimum age requirements can differ between properties on Bookabach, so check the rules of the holiday home in Dorchester you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Dorchester for?
The amount of time you can stay in a Dorchester holiday home for depends on the property. Just enter your travel dates to find options offering extended stays. They feature the things you need to make your extended getaway more comfortable and convenient, such as kitchens and air conditioning. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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