South End holiday rentals

We found 1,003 holiday rentals — enter your dates for availability
Discover a selection of 69 apartments, 14 flats and other holiday rentals in South End that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – South End

Showing deals for:18 Dec - 25 Dec

Dining
Private kitchen
Interior
Interior
Exceptional
(96 reviews)

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

Boston

8% off
AU$15,608
for 7 nights, 1 home
AU$2,230 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

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

Boston

20% off
AU$7,341
for 7 nights, 1 home
AU$1,049 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Outdoor dining
Living area
Room
Private kitchen
Exceptional
(42 reviews)

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

Boston

8% off
AU$7,616
for 7 nights, 1 apartment
AU$1,088 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Interior
Living area
Open Kitchen/Dining Area
Located on floor 2 of a classic Boston 1860's Rowhouse
Exceptional
(89 reviews)

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

Boston

8% off
AU$2,282
for 7 nights, 1 apartment
AU$326 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Room
Isabella Stewart Gardner Museum, Walking distance from Inn
Modern with nice Historic Details, Original Decorative Marble Fireplace
Open Space with Doors available for privacy between Kitchen/ Bedroom
Exceptional
(83 reviews)

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

Boston

8% off
AU$2,282
for 7 nights, 1 apartment
AU$326 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
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
AU$3,781
for 7 nights, 1 apartment
AU$540 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Open Dining with Galley Kitchen
Interior
Newly Refreshed Kitchen, Compact Dishwasher in cabinet under Sink
Located on the adjacent Private way. Outdoor Deck for guest use.
Wonderful
(34 reviews)

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

Boston

8% off
AU$3,745
for 7 nights, 1 apartment
AU$535 per night
includes taxes & fees
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
Open City Loft with sleeper sofa
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Newly Renovated interior of The Boston/Public Library
Fully Open, bright and airy living Space
Exceptional
(85 reviews)

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

Boston

8% off
AU$2,210
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!
Exterior detail
Living area
Interior
Room
Exceptional
(19 reviews)

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

Boston

8% off
AU$2,162
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Private roof deck
Kitchen with granite counter tops and stainless steel appliances
Eat in kitchen
Living room with plenty of natural light.
Exceptional
(190 reviews)

LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

Boston

8% off
AU$3,632
for 7 nights, 1 apartment
AU$519 per night
includes taxes & fees
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

  • 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

Frequently asked questions

When is the best time to visit South End for a holiday rental?
The best time to visit South End, Massachusetts, for a holiday rental is during the peak season, which runs from March to May. This period is particularly vibrant, as the city comes alive with blooming flowers, lively street fairs, and a number of outdoor activities. April, in particular, is a fantastic month to experience the area's charm, with comfortable temperatures averaging around 10 to 15 degrees Celsius, making it ideal for leisurely strolls through the picturesque streets or enjoying a coffee at a local café.As the weather warms up, visitors can fully embrace the region's rich culture, exploring art galleries, historic sites, and the beautiful parks that define the South End. It's a superb time for sightseeing, with plenty of events and festivals that showcase local talent and cuisine.For those looking for more budget-friendly options, November offers a quieter alternative, allowing for a more intimate experience of the city. You can enjoy the area's unique architecture and local shops without the hustle and bustle of peak tourist traffic.
What are the top attractions in South End, Massachusetts, United States of America?
In South End, Massachusetts, visitors can enjoy a variety of attractions that highlight the neighbourhood's rich history and vibrant culture. The area is renowned for its beautiful brownstone buildings and charming streets, which are ideal for leisurely strolls. The Boston Centre for the Arts, located on Tremont Street, showcases a range of contemporary artworks and performances, making it a cultural hub for art enthusiasts.Additionally, the historic Blackstone Square offers a lovely green space, superb for picnics or relaxation amid the urban landscape. South End is also home to the popular SoWa Art + Design District, where visitors can explore art galleries, boutiques, and a bustling farmer's market on Sundays. Food lovers will appreciate the diverse culinary scene, with an array of restaurants and cafes that reflect the neighbourhood's multicultural influences, particularly along Washington Street.For those interested in architecture, the South End's Victorian-style homes and the iconic church of the Church of the Covenant are noteworthy sights.
Are all fees included in the South End 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 South End holiday homes with parking?
Stayz offers a wide selection of holiday homes in South End 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 South End holiday homes?
You can find great discounts on holiday homes in South End 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 South End holiday home booking on Stayz?
To find South End 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 South End?
A long-stay holiday home in South End 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 South End holiday home?
Book your South End 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 South End?
Prices for holiday homes in South End 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 South End 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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