Dorchester holiday rentals
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:8 Jan - 15 Jan
Exceptional
(98 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston
AU$12,772
for 7 nights, 1 home
AU$1,825 per night
includes taxes & fees
Wonderful
(19 reviews)
Newly Renovated Modern Retreat l Near T
Boston
AU$5,911
for 7 nights, 1 apartment
AU$844 per night
includes taxes & fees
Exceptional
(7 reviews)
Premium Loft 3BR&2BA • Heart of Downtown Boston • City Retreat
Boston
AU$6,543
for 7 nights, 1 apartment
AU$935 per night
includes taxes & fees
Exceptional
(34 reviews)
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Boston
AU$6,886
for 7 nights, 1 apartment
AU$984 per night
includes taxes & fees
Exceptional
(21 reviews)
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Boston
AU$4,767
for 7 nights, 1 home
AU$681 per night
includes taxes & fees
Exceptional
(69 reviews)
Spacious Sunlit 3BR • Center of Downtown Boston • Family Favorite
Boston
AU$5,443
for 7 nights, 1 apartment
AU$778 per night
includes taxes & fees
Exceptional
(14 reviews)
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Boston
AU$9,494
for 7 nights, 1 home
AU$1,356 per night
includes taxes & fees
Exceptional
(5 reviews)
Family-Friendly 3BR Apartment Close to Everything
Boston
AU$4,209
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees
Excellent
(7 reviews)
6BR3BA w Parking Near T I Foosball & Family Space
Boston
AU$7,112
for 7 nights, 1 apartment
AU$1,016 per night
includes taxes & fees
Exceptional
(21 reviews)
Modern home-like 3BR2BA Retreat/Minutes to T
Boston
AU$6,004
for 7 nights, 1 home
AU$858 per night
includes taxes & fees
Exceptional
(37 reviews)
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Boston
AU$7,017
for 7 nights, 1 apartment
AU$1,002 per night
includes taxes & fees
Exceptional
(28 reviews)
New Built & Modern 3BR Boston w/ Parking, Pet Friendly near Franklin Park 602
Boston
AU$4,087
for 7 nights, 1 apartment
AU$584 per night
includes taxes & fees
Exceptional
(28 reviews)
3BR2BA Retreat - 2min to Savin Hill Station
Boston
AU$5,698
for 7 nights, 1 apartment
AU$814 per night
includes taxes & fees
Exceptional
(11 reviews)
FREE Parking & Renovated 3BR 2BA Boston • Near Franklin Park & Red Line 558-3
Boston
AU$4,189
for 7 nights, 1 apartment
AU$598 per night
includes taxes & fees
Wonderful
(18 reviews)
Spacious 4BR Boston 1st-floor Apt w/ Free parking • Pet-friendly 301
Boston
AU$3,278
for 7 nights, 1 apartment
AU$468 per night
includes taxes & fees
Exceptional
(47 reviews)
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Boston
AU$6,990
for 7 nights, 1 apartment
AU$999 per night
includes taxes & fees
Exceptional
(35 reviews)
988-Cozy, Lovely and Renovated 4BR-2BA apartment in Boston
Boston
AU$4,721
for 7 nights, 1 apartment
AU$674 per night
includes taxes & fees
Very good
(10 reviews)
3-bedroom apartment in charming Boston/ Near Train
Boston
AU$5,134
for 7 nights, 1 apartment
AU$733 per night
includes taxes & fees
Wonderful
(6 reviews)
74L/2-SPRING GETAWAY EARLY BIRD 10%! Cozy and lovely apartment in Quincy
Quincy
AU$2,818
for 7 nights, 1 apartment
AU$403 per night
includes taxes & fees
Exceptional
(18 reviews)
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Boston
AU$6,698
for 7 nights, 1 home
AU$957 per night
includes taxes & fees
Exceptional
(91 reviews)
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Boston
AU$2,347
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Exceptional
(24 reviews)
Charming 1BR w/ Fireplace Near Fenway & Longwood
Brookline
AU$2,642
for 7 nights, 1 apartment
AU$377 per night
includes taxes & fees
Wonderful
(13 reviews)
Boston Spacious Apartment with private outdoor patio
Boston
AU$6,040
for 7 nights, 1 apartment
AU$863 per night
includes taxes & fees
Exceptional
(83 reviews)
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Boston
AU$2,347
for 7 nights, 1 apartment
AU$335 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
Spacious 4BR Boston 1st-floor Apt w/ Free parking • Pet-friendly 301
Sleeps 12 · 4 bedrooms · 1 bathroom
Beautiful Victorian home, Great view with balcony. Free parking.
Sleeps 9 · 4 bedrooms · 2 bathrooms
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
Super Location Boston 3 1/2,bd. Apt. Driveway Parking
Sleeps 10 · 4 bedrooms · 1 bathroom
Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston!
Sleeps 8 · 3 bedrooms · 2 bathrooms
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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