Holiday rentals near Kenmore Square
We found 2,460 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's close to Kenmore Square. Holiday homes offer the best amenities for you and your friends, family or even pets, such as air conditioning and cable TV. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Kenmore Square
Showing deals for:12 Sept - 19 Sept
Image gallery for Back-Bay 2BR Penthouse w Roof top and GYM
8.48.4 out of 10 rating
Very good
(6 reviews)
Back-Bay 2BR Penthouse w Roof top and GYM
Boston, Massachusetts
16% off
Price is NZ$9,789
NZ$9,789
NZ$1,398 per night
includes taxes & fees
Image gallery for Luxurious apartment in Fenway
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Luxurious apartment in Fenway
Boston, MA
8% off
Price is NZ$12,787
NZ$12,787
NZ$1,827 per night
includes taxes & fees
Image gallery for Historic Townhouse in the Heart of Boston
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Historic Townhouse in the Heart of Boston
Boston, MA
8% off
Price is NZ$9,645
NZ$9,645
NZ$1,378 per night
includes taxes & fees
Image gallery for Fenway 2 bed 2 bath condo
8.88.8 out of 10 rating
Excellent
(5 reviews)
Fenway 2 bed 2 bath condo
Boston, MA
8% off
Price is NZ$12,787
NZ$12,787
NZ$1,827 per night
includes taxes & fees
Image gallery for Cozy 1-bedroom in 2-bedroom apartment in welcoming Boston with WiFi, AC
1010 out of 10 rating
Exceptional
(6 reviews)
Cozy 1-bedroom in 2-bedroom apartment in welcoming Boston with WiFi, AC
Boston, MA
12% off
Price is NZ$4,019
NZ$4,019
NZ$574 per night
includes taxes & fees
Image gallery for Luxury apartment seaport
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Luxury apartment seaport
Boston, MA
8% off
Price is NZ$15,267
NZ$15,267
NZ$2,181 per night
includes taxes & fees
Image gallery for Spacious Triplex with Large backyard FreePrkg
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious Triplex with Large backyard FreePrkg
Boston, MA
8% off
Price is NZ$35,626
NZ$35,626
NZ$5,089 per night
includes taxes & fees
Image gallery for Designer Style 3Br, King Bed, W/D,Parking,Spotless
1010 out of 10 rating
Exceptional
(29 reviews)
Designer Style 3Br, King Bed, W/D,Parking,Spotless
Arlington, MA
8% off
Price is NZ$3,713
NZ$3,713
NZ$530 per night
includes taxes & fees
Image gallery for Comfy & Cozy 2nd level condo walk to MBTA mins to Downtown Boston
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Comfy & Cozy 2nd level condo walk to MBTA mins to Downtown Boston
Boston, MA
8% off
Price is NZ$8,659
NZ$8,659
NZ$1,237 per night
includes taxes & fees
Image gallery for Luxury treat Tuscany style villa just few miles from downtown Boston
1010 out of 10 rating
Exceptional
(5 reviews)
Luxury treat Tuscany style villa just few miles from downtown Boston
Newton, MA
8% off
Price is NZ$31,295
NZ$31,295
NZ$4,471 per night
includes taxes & fees
Image gallery for extended stays
9.69.6 out of 10 rating
Exceptional
(25 reviews)
extended stays
Boston, MA
8% off
Price is NZ$2,973
NZ$2,973
NZ$425 per night
includes taxes & fees
Image gallery for Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
1010 out of 10 rating
Exceptional
(126 reviews)
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
Boston, MA
8% off
Price is NZ$8,762
NZ$8,762
NZ$1,252 per night
includes taxes & fees
Image gallery for Beautiful Dorchester Home in Boston!
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Dorchester Home in Boston!
Boston, MA
8% off
Price is NZ$7,247
NZ$7,247
NZ$1,035 per night
includes taxes & fees
Image gallery for Spacious 2 bdrm apartment 1.8 mils from Harvard Sq
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious 2 bdrm apartment 1.8 mils from Harvard Sq
Watertown, MA
8% off
Price is NZ$4,728
NZ$4,728
NZ$675 per night
includes taxes & fees
Image gallery for 14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton
9.69.6 out of 10 rating
Exceptional
(5 reviews)
14/1 - SPRING GETAWAY EARLY BIRD 10%! 3-bedroom apartment in peaceful Milton
Milton, MA
8% off
Price is NZ$4,264
NZ$4,264
NZ$609 per night
includes taxes & fees
Image gallery for 60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
9.49.4 out of 10 rating
Exceptional
(8 reviews)
60/3 - SPRING GETAWAY 10% OFF !Newly built & cozy apartment in Boston
Boston, MA
8% off
Price is NZ$5,289
NZ$5,289
NZ$756 per night
includes taxes & fees
Image gallery for Stylish Studio - ✓Sanitized ✓Private ✓Spotless
1010 out of 10 rating
Exceptional
(5 reviews)
Stylish Studio - ✓Sanitized ✓Private ✓Spotless
Arlington, MA
8% off
Price is NZ$1,742
NZ$1,742
NZ$249 per night
includes taxes & fees
Image gallery for Grand piano Apt near T station towards downtown Boston, TD Garden and Hospitals.
9.49.4 out of 10 rating
Exceptional
(67 reviews)
Grand piano Apt near T station towards downtown Boston, TD Garden and Hospitals.
Medford, MA
6% off
Price is NZ$2,813
NZ$2,813
NZ$402 per night
includes taxes & fees
Image gallery for Perfect for large group 10 beds• 4.6 mi to Downtown •steps to T 5BD/2Bth
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Perfect for large group 10 beds• 4.6 mi to Downtown •steps to T 5BD/2Bth
Boston, MA
8% off
Price is NZ$9,835
NZ$9,835
NZ$1,405 per night
includes taxes & fees
Image gallery for 25% discount August! Luxury House, Fenced Yard, Short Walk to Harvard. Dogs OK.
9.89.8 out of 10 rating
Exceptional
(117 reviews)
25% discount August! Luxury House, Fenced Yard, Short Walk to Harvard. Dogs OK.
Cambridge, MA
8% off
Price is NZ$7,546
NZ$7,546
NZ$1,078 per night
includes taxes & fees
Image gallery for Sunny 2 bedroom in Southie
1010 out of 10 rating
Exceptional
(6 reviews)
Sunny 2 bedroom in Southie
Boston, MA
15% off
Price is NZ$6,996
NZ$6,996
NZ$999 per night
includes taxes & fees
Image gallery for Unique Cathedral Ceiling Condo W/D, Parking
1010 out of 10 rating
Exceptional
(8 reviews)
Unique Cathedral Ceiling Condo W/D, Parking
Arlington, MA
8% off
Price is NZ$3,415
NZ$3,415
NZ$488 per night
includes taxes & fees
Image gallery for A Cozy 5BR Apartment near Harvard Square and MIT
9.89.8 out of 10 rating
Exceptional
(38 reviews)
A Cozy 5BR Apartment near Harvard Square and MIT
Cambridge, MA
8% off
Price is NZ$8,862
NZ$8,862
NZ$1,266 per night
includes taxes & fees
Image gallery for A beautiful 3BR Apartment near Harvard and MIT
9.69.6 out of 10 rating
Exceptional
(40 reviews)
A beautiful 3BR Apartment near Harvard and MIT
Cambridge, MA
8% off
Price is NZ$4,941
NZ$4,941
NZ$706 per night
includes taxes & fees
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Find the best place to stay - Kenmore Square
Maverick Suites at 28 Fenway
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
215 reviews(215 reviews)
Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway
Sleeps 2 · 1 bathroom
8.88.8 out of 10
Excellentexcellent
243 reviews(243 reviews)
Hidden Gem right in the city of Boston!
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Stylish, Comfortable Luxury | Near T
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
4 reviews(4 reviews)
Great Apartment on River/ Harvard Square two blocks
Sleeps 5 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
10 reviews(10 reviews)
Relax with family or friends to this elegant apartment in the heart of Waltham
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
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