Dorchester holiday rentals
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
Exceptional
(90 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston
AU$17,423
for 7 nights, 1 home
AU$2,489 per night
includes taxes & fees
Exceptional
(28 reviews)
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Boston
AU$6,793
for 7 nights, 1 apartment
AU$970 per night
includes taxes & fees
Exceptional
(21 reviews)
Modern home-like 3BR2BA Retreat/Minutes to T
Boston
AU$5,924
for 7 nights, 1 home
AU$846 per night
includes taxes & fees
Very good
(6 reviews)
6BR3BA w Parking Near T I Foosball & Family Space
Boston
AU$7,016
for 7 nights, 1 apartment
AU$1,002 per night
includes taxes & fees
Exceptional
(6 reviews)
3-bedroom 2 baths beautiful victorian with WiFi, AC
Boston
AU$6,520
for 7 nights, 1 apartment
AU$931 per night
includes taxes & fees
Exceptional
(49 reviews)
World Cup 4BR Near Downtown Boston Parking & 1-Min Walk to Train
Boston
AU$5,601
for 7 nights, 1 apartment
AU$800 per night
includes taxes & fees
Wonderful
(19 reviews)
Newly Renovated Modern Retreat l Near T
Boston
AU$5,833
for 7 nights, 1 apartment
AU$833 per night
includes taxes & fees
Exceptional
(46 reviews)
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Boston
AU$6,894
for 7 nights, 1 apartment
AU$985 per night
includes taxes & fees
Exceptional
(12 reviews)
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Boston
AU$5,969
for 7 nights, 1 apartment
AU$853 per night
includes taxes & fees
Exceptional
(37 reviews)
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Boston
AU$6,922
for 7 nights, 1 apartment
AU$989 per night
includes taxes & fees
Exceptional
(26 reviews)
3BR2BA Retreat - 2min to Savin Hill Station
Boston
AU$5,623
for 7 nights, 1 apartment
AU$803 per night
includes taxes & fees
Excellent
(9 reviews)
3-bedroom apartment in charming Boston/ Near Train
Boston
AU$5,066
for 7 nights, 1 apartment
AU$724 per night
includes taxes & fees
Exceptional
(23 reviews)
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Boston
AU$4,794
for 7 nights, 1 apartment
AU$685 per night
includes taxes & fees
Exceptional
(66 reviews)
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Boston
AU$7,490
for 7 nights, 1 apartment
AU$1,070 per night
includes taxes & fees
Exceptional
(87 reviews)
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Boston
AU$2,307
for 7 nights, 1 apartment
AU$330 per night
includes taxes & fees
Exceptional
(21 reviews)
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Cambridge
AU$3,687
for 7 nights, 1 home
AU$527 per night
includes taxes & fees
Exceptional
(83 reviews)
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Boston
AU$2,307
for 7 nights, 1 apartment
AU$330 per night
includes taxes & fees
Exceptional
(5 reviews)
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Boston
AU$3,822
for 7 nights, 1 apartment
AU$546 per night
includes taxes & fees
Exceptional
(85 reviews)
Fresh Modern City Loft Apt! Easy Access to the city!
Boston
AU$2,235
for 7 nights, 1 apartment
AU$319 per night
includes taxes & fees
Exceptional
(18 reviews)
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Boston
AU$2,186
for 7 nights, 1 apartment
AU$312 per night
includes taxes & fees
Exceptional
(39 reviews)
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Boston
AU$7,700
for 7 nights, 1 apartment
AU$1,100 per night
includes taxes & fees
Exceptional
(39 reviews)
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
Boston
AU$4,158
for 7 nights, 1 apartment
AU$594 per night
includes taxes & fees
Exceptional
(5 reviews)
Family-Friendly 3BR Apartment Close to Everything
Boston
AU$4,153
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
Wonderful
(34 reviews)
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
Boston
AU$3,786
for 7 nights, 1 apartment
AU$541 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Dorchester
John F. Kennedy Presidential Library and Museum
More information about John F. Kennedy Presidential Library and Museum. Opens in a new window.Find the best place to stay - Dorchester
14a-Cozy and well decorated apartment in awesome Boston
Sleeps 13 · 3 bedrooms · 1+ bathroom
Spacious 4BR Boston 1st-floor Apt w/ Free parking • Pet-friendly 301
Sleeps 12 · 4 bedrooms · 1 bathroom
II New apartment with Luxury amenities in Boston
Sleeps 4 · 2 bedrooms · 1 bathroom
Spacious and Clean 2 Bedroom in Dorchester Neighborhood of Boston
Sleeps 4 · 2 bedrooms · 1 bathroom
30/3-SPRING GETAWAY 10% OFF! Newly renovated, cozy, airy apartment in Boston
Sleeps 10 · 3 bedrooms · 1 bathroom
Spacious, New Renovation | Near T
Sleeps 18 · 6 bedrooms · 3+ bathrooms
Top rated rentals - Dorchester
Modern and charming in a great location
We were a large family group and the apartment was very comfortable. The location is excellent, easy to walk to the train station, shops etc.
Andrew R.
Stayed Oct 2024
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
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 Stayz?
Stayz 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?
Stayz 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 Stayz, 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 Stayz?
To find Dorchester holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?
Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in Dorchester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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