Holiday rentals near Kenmore Square
We found 2,505 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:14 Nov - 21 Nov
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(77 reviews)
Beautiful Boston Brownstone!
Boston, MA
8% off
Price is S$5,235
S$5,235
S$748 per night
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
9.49.4 out of 10 rating
Exceptional
(15 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
15% off
Price is S$3,238
S$3,238
S$463 per night
includes taxes & fees
Image gallery for Modern 2BR/ Close to Boston with a lovely outdoor space
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Modern 2BR/ Close to Boston with a lovely outdoor space
Melrose, MA
8% off
Price is S$2,710
S$2,710
S$387 per night
includes taxes & fees
Image gallery for West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
9.89.8 out of 10 rating
Exceptional
(63 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
14% off
Price is S$3,523
S$3,523
S$503 per night
includes taxes & fees
Image gallery for 39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
9.69.6 out of 10 rating
Exceptional
(44 reviews)
39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
Quincy, MA
15% off
Price is S$3,131
S$3,131
S$447 per night
includes taxes & fees
Image gallery for Spacious Triplex with Large backyard FreePrkg
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Spacious Triplex with Large backyard FreePrkg
Boston, MA
8% off
Price is S$32,280
S$32,280
S$4,611 per night
includes taxes & fees
Image gallery for 76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
9.69.6 out of 10 rating
Exceptional
(7 reviews)
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Boston, MA
12% off
Price is S$4,347
S$4,347
S$621 per night
includes taxes & fees
Image gallery for Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Medford, MA
15% off
Price is S$2,165
S$2,165
S$309 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
(41 reviews)
A Cozy 5BR Apartment near Harvard Square and MIT
Cambridge, MA
8% off
Price is S$6,370
S$6,370
S$910 per night
includes taxes & fees
Image gallery for SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
9.69.6 out of 10 rating
Exceptional
(26 reviews)
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
Boston, MA
15% off
Price is S$2,783
S$2,783
S$398 per night
includes taxes & fees
Image gallery for Great Apartment on River/ Harvard Square two blocks
9.09.0 out of 10 rating
Wonderful
(17 reviews)
Great Apartment on River/ Harvard Square two blocks
Cambridge, MA
8% off
Price is S$2,128
S$2,128
S$304 per night
includes taxes & fees
Image gallery for Adams Village 6-Bed Apt: City Perks, Suburban Vibe
8.68.6 out of 10 rating
Excellent
(8 reviews)
Adams Village 6-Bed Apt: City Perks, Suburban Vibe
Boston, MA
8% off
Price is S$5,503
S$5,503
S$786 per night
includes taxes & fees
Image gallery for Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Boston Luxury Home, Free parking, 5 mins to the Casino, 10 minutes to airport.
Everett, MA
8% off
Price is S$2,659
S$2,659
S$380 per night
includes taxes & fees
Image gallery for Travelers Choice Best of Boston Houseboat Suite 2!
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Travelers Choice Best of Boston Houseboat Suite 2!
Boston, MA
8% off
Price is S$3,933
S$3,933
S$562 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Condo Bos Common Downtown
1010 out of 10 rating
Exceptional
(6 reviews)
Back-Bay Upscale Central Condo Bos Common Downtown
Boston, MA
7% off
Price is S$5,715
S$5,715
S$816 per night
includes taxes & fees
Image gallery for 284-Cozy House with free huge parking
9.89.8 out of 10 rating
Exceptional
(67 reviews)
284-Cozy House with free huge parking
Quincy, MA
15% off
Price is S$4,605
S$4,605
S$658 per night
includes taxes & fees
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, MA
15% off
Price is S$5,053
S$5,053
S$722 per night
includes taxes & fees
Image gallery for Historic Private Auburndale Retreat Near Boston!
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Historic Private Auburndale Retreat Near Boston!
Newton, MA
7% off
Price is S$1,974
S$1,974
S$282 per night
includes taxes & fees
Image gallery for Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown
Boston, MA
8% off
Price is S$4,281
S$4,281
S$612 per night
includes taxes & fees
Image gallery for Modern 3BR/ Close to Encore- Everett #2
8.88.8 out of 10 rating
Excellent
(28 reviews)
Modern 3BR/ Close to Encore- Everett #2
Everett, MA
8% off
Price is S$2,310
S$2,310
S$330 per night
includes taxes & fees
Image gallery for Newly Renovated Modern Retreat l Near T
9.09.0 out of 10 rating
Wonderful
(14 reviews)
Newly Renovated Modern Retreat l Near T
Boston, MA
5% off
Price is S$5,325
S$5,325
S$761 per night
includes taxes & fees
Image gallery for Stunning South End/Back Bay Penthouse!
1010 out of 10 rating
Exceptional
(89 reviews)
Stunning South End/Back Bay Penthouse!
Boston, MA
8% off
Price is S$5,801
S$5,801
S$829 per night
includes taxes & fees
Image gallery for Cody's Place Winthrop Boston Logan Airport Beaches
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Cody's Place Winthrop Boston Logan Airport Beaches
Winthrop, MA
15% off
Price is S$2,015
S$2,015
S$288 per night
includes taxes & fees
Image gallery for Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!
Revere, MA
8% off
Price is S$3,652
S$3,652
S$522 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
8.88.8 out of 10
Excellentexcellent
255 reviews(255 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
The Pistachio Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Historic Townhouse in the Heart of Boston
Sleeps 7 · 3 bedrooms · 1+ bathroom
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Back-Bay Lux Central 2BR Condo with Rooftop and Parking
Sleeps 6 · 2 bedrooms · 2 bathrooms
Tranquil Renovated 3BR Allston Condo + Parking , Close to Harvard/BU/BC/MIT!
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
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