Dorchester holiday lettings

We found 1,521 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

Dining
Private kitchen
Interior
Interior
Exceptional
(90 reviews)

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

Boston

8% off
£9,678
for 7 nights, 1 home
£1,383 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Living area
Private kitchen
Living area
Room
Exceptional
(28 reviews)

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

Boston

7% off
£3,753
for 7 nights, 1 apartment
£536 per night
includes taxes & fees
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Private kitchen
Interior
Interior
Deck Off of Kitchen
Exceptional
(13 reviews)

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

Boston

19% off
£4,651
for 7 nights, 1 home
£664 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Interior
Interior
Room
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
£3,170
for 7 nights, 1 home
£453 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Room
Interior
Dining
Private kitchen
Very good
(6 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

7% off
£3,800
for 7 nights, 1 apartment
£543 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Interior
Living area
Interior
Dining
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
£3,104
for 7 nights, 1 apartment
£443 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Dining
Cool Historic Details in this 1860's townhome apartment,  stairs required!
Bedroom 2,
Master Bath Views
Exceptional
(46 reviews)

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

Boston

7% off
£3,843
for 7 nights, 1 apartment
£549 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Living area
Exterior detail
Interior
Private kitchen
Exceptional
(6 reviews)

3-bedroom 2 baths beautiful victorian with WiFi, AC

Boston

8% off
£3,464
for 7 nights, 1 apartment
£495 per night
includes taxes & fees
3-bedroom 2 baths beautiful victorian with WiFi, AC
Interior
Private kitchen
Living area
Dining
Exceptional
(23 reviews)

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

Boston

8% off
£2,562
for 7 nights, 1 apartment
£366 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Outdoor private space
Interior
Room
Living area
Exceptional
(49 reviews)

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

Boston

9% off
£2,980
for 7 nights, 1 apartment
£426 per night
includes taxes & fees
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Private kitchen
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
£3,179
for 7 nights, 1 apartment
£454 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Interior
Interior
Room
Private kitchen
Exceptional
(26 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
£2,978
for 7 nights, 1 apartment
£425 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Steps Required.
Dining
Interior
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

7% off
£3,859
for 7 nights, 1 apartment
£551 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
£2,689
for 7 nights, 1 apartment
£384 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Terrace/patio
Room
Dining
Private kitchen
Exceptional
(21 reviews)

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

Cambridge

15% off
£2,028
for 7 nights, 1 home
£290 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Open Kitchen/Dining Area
Living area
Located on floor 2 of a classic Boston 1860's Rowhouse
Entrance/steps to apartment. Please note,  steps required
Exceptional
(87 reviews)

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

Boston

7% off
£1,233
for 7 nights, 1 apartment
£176 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
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
£3,886
for 7 nights, 1 apartment
£555 per night
includes taxes & fees
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Room
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

7% off
£1,233
for 7 nights, 1 apartment
£176 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Open City Loft with sleeper sofa
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Fully Open,  bright and airy living Space
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

7% off
£1,195
for 7 nights, 1 apartment
£171 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!
Interior
Exterior detail
Living area
Open Kitchen
Exceptional
(5 reviews)

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

Boston

8% off
£2,058
for 7 nights, 1 apartment
£294 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Living area
Living area
Room
Outdoor dining
Exceptional
(39 reviews)

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

Boston

7% off
£4,290
for 7 nights, 1 apartment
£613 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Exterior detail
Living area
Room
Interior
Exceptional
(18 reviews)

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

Boston

7% off
£1,178
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Interior
Exterior detail
Room
Interior
Exceptional
(39 reviews)

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

Boston

8% off
£2,205
for 7 nights, 1 apartment
£315 per night
includes taxes & fees
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
you’ll find all the basics you need for a comfortable stay.
Room
With stylish touches, cozy seating, and plenty of room to unwind
The living room is thoughtfully designed, offering a warm & inviting atmosphere.
Exceptional
(5 reviews)

Family-Friendly 3BR Apartment Close to Everything

Boston

8% off
£2,201
for 7 nights, 1 apartment
£314 per night
includes taxes & fees
Family-Friendly 3BR Apartment Close to Everything
  • 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, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Dorchester

  • Rich Cultural Heritage: Discover the area's history at the Dorchester Antiquarian, showcasing local artefacts and stories.
  • Scenic Parks: Enjoy outdoor activities in lush parks, perfect for relaxation and family outings.
  • Charming Streets: Stroll through the picturesque streets of Dorchester Centre, filled with unique shops and local character.
  • Historic Churches: Visit beautiful historic churches that reflect the neighbourhood's diverse community.
  • Welcoming Community: Experience the warm hospitality of Dorchester's friendly residents, enhancing your stay.

Popular types of accommodation around Dorchester

Welcome to Dorchester, a vibrant neighbourhood in Boston, Massachusetts, where rich history meets modern charm. Explore local parks, cultural landmarks, and unique dining experiences that reflect the area’s diverse heritage. When it comes to accommodation, you'll find a variety of options including houses, spacious apartments, and comfortable condos, perfect for your stay. Discover the ideal apartment in Dorchester and immerse yourself in all the local attractions this lively community has to offer.

  • Houses: Ideal for families or groups, these homes provide a comfortable and spacious environment, allowing guests to enjoy a home-like atmosphere during their stay in Dorchester.
  • Apartments: A popular choice for couples or solo travellers, offering convenience and access to local amenities in a compact living space.
  • Condos: These modern units often feature shared facilities and are perfect for those seeking a blend of community and privacy.
  • Cottages: Quaint and charming, these properties provide a cosy retreat for those looking to unwind in a picturesque setting.
  • House Boats: For a unique experience, consider staying on a houseboat, which offers a delightful blend of water views and comfort.**

Top attractions in and around Dorchester

Dorchester, a vibrant neighbourhood in Boston, Massachusetts, offers a delightful mix of family-friendly activities and cultural experiences. Visitors can explore urban parks, historic churches, and charming streets, all rich in local heritage. Don't miss the Dorchester Antiquarian for a taste of the area's history. This community is perfect for those seeking outdoor adventures and city-themed explorations, ensuring a memorable stay filled with diverse attractions and experiences.

  • John F. Kennedy Presidential Library and Museum: This cultural gem offers an insightful journey through the life and legacy of President Kennedy. Set on a stunning waterfront, the museum features interactive exhibits, historical documents, and a beautiful garden, making it a must-visit for those interested in American history.
  • Fenway Park: Although located a few miles away, this iconic sports stadium is steeped in baseball history. Catching a game here is a thrilling experience, surrounded by passionate fans and the vibrant atmosphere of America’s pastime.
  • Boston Common: This expansive urban park, not far from Dorchester, is perfect for family outings. Enjoy leisurely strolls, picnics, and outdoor activities amidst lush greenery and historic monuments, offering a relaxing escape in the heart of the city.

Things to do recommended for couples

Discover the charm of Dorchester with a leisurely walk along the Neponset River. Enjoy a cosy picnic at Franklin Park, or indulge in a romantic dinner at a local bistro. Don’t miss the vibrant murals in the area, perfect for a couple’s photo opportunity.

Things to do recommended for families

Families visiting Dorchester can explore the Franklin Park Zoo, where children can meet exotic animals, or enjoy a day at the nearby Boston Nature Centre, offering hands-on activities. Don’t miss the interactive exhibits at the Boston Children's Museum for a fun-filled experience.

Things to do recommended for groups

Groups visiting Dorchester can enjoy a stroll through the scenic Franklin Park, experience the vibrant murals in the local art scene, and savour delicious cuisine at diverse eateries. Don't miss a visit to the historic John F. Kennedy Presidential Library for an enriching cultural experience.

*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

If you're travelling with a group, family, pets, or planning a longer stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Dorchester with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Dorchester with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as to seek out suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Dorchester: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Dorchester: If you're seeking holiday rentals with offers 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 rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Dorchester

Dorchester, a vibrant neighbourhood in Boston, Massachusetts, offers a rich tapestry of cultural experiences and family-friendly attractions. From scenic parks to historic landmarks, visitors can immerse themselves in the local vibe. Explore the charming streets of Dorchester Centre, enjoy the lush greenery in South Dorchester, and savour the warm hospitality of its friendly residents. Whether you're seeking history or relaxation, Dorchester promises a delightful and enriching getaway.

  • Boston: Boston is a vibrant metropolis that serves as the core of Dorchester. Visitors flock to this historic city for its rich cultural experiences, family-friendly attractions, and city-themed adventures. Explore renowned educational institutions, indulge in music concerts, or enjoy a day of shopping at bustling mall centres. Key landmarks include famous sports stadiums and event venues that host a variety of conferences and entertainment options, making it a must-visit destination for travellers seeking a dynamic urban experience.
  • Downtown Boston: Located approximately 6km from Dorchester, Downtown Boston is an energetic neighbourhood that attracts families, business travellers, and city explorers alike. Here, you'll find a plethora of shopping centres, educational opportunities, and an array of culinary delights. The area is rich in attractions, including historic sports stadiums and urban parks perfect for relaxation. This central hub is ideal for those looking to immerse themselves in the city's pulse while enjoying a mix of leisure and business activities.
  • Meeting House Hill: Just 322m from Dorchester, Meeting House Hill offers a charming blend of outdoor activities, cultural experiences, and family-friendly venues. This neighbourhood is perfect for those seeking arena entertainment, motor racing, and educational experiences. Notable local landmarks include urban parks and historic sites that invite exploration, as well as event venues that host various occasions. Meeting House Hill combines a welcoming community vibe with ample opportunities for leisure and enjoyment.

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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, please utilise our filters to search by price, location, and type of accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides an excellent platform for planning new adventures, refining your travel arrangements, or managing your existing bookings. Your saved or reserved properties are conveniently organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

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, 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.
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, 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.
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.

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