Jackson Square Station Vacation Rentals

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Our top choices for Jackson Square Station vacation homes

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T
Roxbury
9.4 out of 10, Exceptional, (23 reviews)
"This house was exactly what we needed for our girls weekend! Great location, roomy living area, host communication was wonderful. "
United States
Brooke S.
Clean, Contemporary Escape | Near T

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

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fenway–Kenmore
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for large groups."
United States
Jason Y.
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Essential Boston Home | Near South End

Essential Boston Home | Near South End
Roxbury
9.8 out of 10, Exceptional, (13 reviews)
"Everything was clean and the check in/check out process was very easy! The location was great and the size/amenities are perfect for our girls’ weekend in Boston. "
United States
Katie M.
Essential Boston Home | Near South End

Cozy Apartment | Near T

Cozy Apartment | Near T
Roxbury
9.0 out of 10, Wonderful, (26 reviews)
"House was nice, beds were incredibly comfortable"
United States
Andrew K.
Cozy Apartment | Near T

Family & Group Haven near Downtown Retreat

Family & Group Haven near Downtown Retreat
Dorchester
8.6 out of 10, Excellent, (13 reviews)
"House is super clean, easy parking. "
Canada
Jake
Family & Group Haven near Downtown Retreat

Spacious 6BR 2unit near Downtown

Spacious 6BR 2unit near Downtown
Dorchester
9.0 out of 10, Wonderful, (4 reviews)
"His home was awesome. It had everything our large group needed and was as advertised. We enjoyed our stay and would definitely come back again. "
United States
Matthew C.
Spacious 6BR 2unit near Downtown

Cozy Boston Condo | Near T

Cozy Boston Condo | Near T
Roxbury
9.6 out of 10, Exceptional, (12 reviews)
"Beautiful clean home and excellent responsive host. Thank you for a great stay. "
United States
Dania B.
Cozy Boston Condo | Near T

Lovely 2 bedroom condo 5 mins from downtown

Lovely 2 bedroom condo 5 mins from downtown
Roxbury
5.6 out of 10, (4 reviews)
"Good. Part of neighborhood was a little sketchy. Good to get downtown."
United States
Greg S.
The price is CA $552
CA $1,174 total
includes taxes & fees
Feb 21 - Feb 22
Lovely 2 bedroom condo 5 mins from downtown

Spacious 5BR Near Downtown – Walk to Subway, Balcony, Near Beach

Spacious 5BR Near Downtown – Walk to Subway, Balcony, Near Beach
Dorchester
8.8 out of 10, Excellent, (8 reviews)
"It was a spacious and awesome location for 10 people. Very cozy and in an area that was central and walking distance to cool restaurants and bars. "
United States
Leah G.
Spacious 5BR Near Downtown – Walk to Subway, Balcony, Near Beach

Cozy Duplex | Near T

Cozy Duplex | Near T
Roxbury
9.8 out of 10, Exceptional, (10 reviews)
"Great Property and very well equipped. Thank you!"
United States
Emily M.
Cozy Duplex | Near T

Expansive Essential Triplex | near T

Expansive Essential Triplex | near T
Roxbury
9.4 out of 10, Exceptional, (3 reviews)
"Everything was clean and easy to navigate. I needed to contact the host with a question and got an immediate response. "
United States
Dale N.
Expansive Essential Triplex | near T

Cozy Oasis | Near South End

Cozy Oasis | Near South End
Roxbury
10.0 out of 10, Exceptional, (3 reviews)
"Lots of space and beds, comfortably fit 8 adults. Easy process, no issues on check in or check out. Thanks!"
United States
Adam K.
Cozy Oasis | Near South End

City's Hippest Neighborhood.

City's Hippest Neighborhood.
Jamaica Plain
10.0 out of 10, Exceptional, (102 reviews)
"Fantastic place in a wonderful neighborhood. "
United States
MARY DIANE S.
City's Hippest Neighborhood.

NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!

NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
Roxbury
10.0 out of 10, Exceptional, (5 reviews)
"This is a lovely place to stay with you and your friends"
United States
Emily H.
The price is CA $437
CA $1,242 total
includes taxes & fees
Feb 20 - Feb 21
NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!

Brand-new spacious 4 bedroom home, minutes from train station, free st parking

Brand-new spacious 4 bedroom home, minutes from train station, free st parking
Dorchester
8.6 out of 10, Excellent, (19 reviews)
"Convenient and spacious home perfect for our large family. The host was responsive to questions and check in/out was quick and easy. "
United States
Sarah K.
Brand-new spacious 4 bedroom home, minutes from train station, free st parking

Park-Side Home in Jamaica Plain

Park-Side Home in Jamaica Plain
Jamaica Plain
9.8 out of 10, Exceptional, (6 reviews)
"Great place for a family. Close to the city. Had everything we needed. Nice kitchen and in-house laundry. Host communication was easy and minor issues were quickly resolved with no fuss."
United States
James D.
Park-Side Home in Jamaica Plain

Single family home close to universities and and major hospitals.

Single family home close to universities and and major hospitals.
Roxbury
10.0 out of 10, Exceptional, (1 review)
"Can’t wait to come back"
United States
Terry C.
Single family home close to universities and and major hospitals.

New-Group stay mins from DowntownConvention BeachFenway FreePrkg

New-Group stay mins from DowntownConvention BeachFenway FreePrkg
Dorchester
New-Group stay mins from DowntownConvention BeachFenway FreePrkg

Enjoy Boston, Private Patio On Montgomery Park

Enjoy Boston, Private Patio On Montgomery Park
South End
7.4 out of 10, Good, (3 reviews)
"Wonderful location and property. The lovely garden is fantastic. Would definitely recommend this to anyone wanting to experience the best of Boston. "
United States
Jennifer G.
Enjoy Boston, Private Patio On Montgomery Park

Family House with yard at prime location

Family House with yard at prime location
Jamaica Plain
10.0 out of 10, Exceptional, (3 reviews)
"We spent a couple days seeing the sites in Boston and this house was a great “home base” it was close to transit so we could easily get downtown and the property itself was clean and well appointed."
United States
Laurie M.
Family House with yard at prime location
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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What types of Vacation Homes can I find in Jackson Square Station?

When you’re looking for Jackson Square Station Vacation Homes in 2026, you can use Expedia’s filters to find accommodation that’s family-friendly or business-friendly, and narrow down your search results by amenities, price per night, and much more. For example, you can search for Vacation Homes that welcome pets, or one with accessibility features. You’ll find a range of places to stay to suit every budget, so if you're looking for cheap Vacation Homes in Jackson Square Station, use our simple search function to help you secure a good deal. If the exact location of Vacation Homes is important to you, try our map facility to view available places in relation to each other and to Jackson Square Station.

How much do Vacation Homes cost in Jackson Square Station?

Prices for Jackson Square Station Vacation Homes can start from as little as * in 2026. The cost per night varies depending on several factors, including the amenities on offer at Vacation Homes, the exact location of Vacation Homes and how far they are from Jackson Square Station, as well as how high the demand for accommodation is near Jackson Square Station on the dates of your booking. At Expedia, we cater for every budget, so if you’re looking for cheap Vacation Homes in Jackson Square Station, you can sleep easy knowing that we’ll help you to secure some of the very best deals on offer.

How to find the best deals on Jackson Square Station Vacation Homes?

Expedia’s search function can help you find a great deal on Jackson Square Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Jackson Square Station at a glance. If you have a specific price range in mind, try selecting minimum and maximum prices per night to narrow your results. You can also filter by guest ratings and star ratings to find some of the best offers for Vacation Homes within your budget. Don’t forget, if you’re an Expedia Rewards member, you can use the ‘Member Prices’ filter to make instant savings on your booking.

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One of the many benefits of booking Jackson Square Station Vacation Homes with Expedia is the clear and simple search function. When you use the many filters on offer, you can easily compile a shortlist of fantastic places to stay, and make comparisons between the different Vacation Homes so that you can choose exactly what you need. At Expedia, it’s possible to create your own customized package and make great savings by booking flights, car hire, and more at the same time as Jackson Square Station Vacation Homes. And don’t forget that with free membership to Expedia Rewards, you can earn points on all eligible purchases, and build your points total to use towards future travel.

What is the cancellation policy on booking Jackson Square Station Vacation Homes?

It’s often possible to change or cancel bookings at Jackson Square Station Vacation Homes without a fee, but it depends on the rules and restrictions of the various Vacation Homes. Many booking options offer a window of flexibility, for example a full refund if you cancel more than 24 or 48 hours before Jackson Square Station arrival dates. It’s best to check the policies of the individual Vacation Homes before making a booking, if flexibility is important to you. You can filter for the ‘Fully refundable’ payment type when you search for Vacation Homes. You can also view the terms of the different Vacation Homes at any time by checking the details of your booking at Expedia.

*Prices and availability are subject to change. Additional terms may apply 

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