Holiday rentals near Kenmore Square
We found 2,497 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:31 Oct - 7 Nov
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(76 reviews)
Beautiful Boston Brownstone!
Boston, MA
8% off
Price is NZ$7,225
NZ$7,225
NZ$1,032 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
(62 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
14% off
Price is NZ$4,646
NZ$4,646
NZ$664 per night
includes taxes & fees
Image gallery for Spacious Triplex with Large backyard FreePrkg
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Spacious Triplex with Large backyard FreePrkg
Boston, MA
8% off
Price is NZ$41,115
NZ$41,115
NZ$5,874 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
(43 reviews)
39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
Quincy, MA
8% off
Price is NZ$4,554
NZ$4,554
NZ$651 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Condo Bos Common Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Back-Bay Upscale Central Condo Bos Common Downtown
Boston, Massachusetts
8% off
Price is NZ$8,854
NZ$8,854
NZ$1,265 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, Massachusetts
15% off
Price is NZ$7,856
NZ$7,856
NZ$1,122 per night
includes taxes & fees
Image gallery for Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
8.48.4 out of 10 rating
Very good
(6 reviews)
Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
Boston, MA
8% off
Price is NZ$10,218
NZ$10,218
NZ$1,460 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$7,960
NZ$7,960
NZ$1,137 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
8% off
Price is NZ$4,040
NZ$4,040
NZ$577 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 NZ$5,730
NZ$5,730
NZ$819 per night
includes taxes & fees
Image gallery for Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
1010 out of 10 rating
Exceptional
(64 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston, MA
8% off
Price is NZ$19,339
NZ$19,339
NZ$2,763 per night
includes taxes & fees
Image gallery for 2nd Floor Apartment 5 minutes to the subway to Boston & Cambridge.
1010 out of 10 rating
Exceptional
(5 reviews)
2nd Floor Apartment 5 minutes to the subway to Boston & Cambridge.
Boston, MA
8% off
Price is NZ$1,953
NZ$1,953
NZ$279 per night
includes taxes & fees
Image gallery for 1-Bedroom Apartment in Milton Lower Mills convenient to Boston & Cambridge
9.49.4 out of 10 rating
Exceptional
(12 reviews)
1-Bedroom Apartment in Milton Lower Mills convenient to Boston & Cambridge
Boston, MA
8% off
Price is NZ$1,953
NZ$1,953
NZ$279 per night
includes taxes & fees
Image gallery for Stylish Boston Renovation | Near T
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Stylish Boston Renovation | Near T
Boston, Massachusetts
20% off
Price is NZ$6,738
NZ$6,738
NZ$963 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$7,338
NZ$7,338
NZ$1,048 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 NZ$6,681
NZ$6,681
NZ$954 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 NZ$7,199
NZ$7,199
NZ$1,028 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 NZ$8,513
NZ$8,513
NZ$1,216 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
6% off
Price is NZ$6,040
NZ$6,040
NZ$863 per night
includes taxes & fees
Image gallery for Travelers Choice Best of Boston Houseboat Suite 2!
9.89.8 out of 10 rating
Exceptional
(43 reviews)
Travelers Choice Best of Boston Houseboat Suite 2!
Boston, MA
8% off
Price is NZ$5,183
NZ$5,183
NZ$740 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 NZ$2,765
NZ$2,765
NZ$395 per night
includes taxes & fees
Image gallery for Waterfront. Boston & island views. Kayaks onsite Weekly discount Fall dates now!
9.49.4 out of 10 rating
Exceptional
(127 reviews)
Waterfront. Boston & island views. Kayaks onsite Weekly discount Fall dates now!
Quincy, MA
8% off
Price is NZ$2,769
NZ$2,769
NZ$396 per night
includes taxes & fees
Image gallery for Great Apartment on River/ Harvard Square two blocks
8.88.8 out of 10 rating
Excellent
(16 reviews)
Great Apartment on River/ Harvard Square two blocks
Cambridge, MA
8% off
Price is NZ$2,804
NZ$2,804
NZ$401 per night
includes taxes & fees
Image gallery for Spacious Private Retreat Near Downtown Boston!
1010 out of 10 rating
Exceptional
(10 reviews)
Spacious Private Retreat Near Downtown Boston!
Newton, MA
7% off
Price is NZ$5,709
NZ$5,709
NZ$816 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
250 reviews(250 reviews)
Hidden Gem right in the city of Boston!
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Stylish, Comfortable Luxury Near T
Sleeps 8 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 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
62 reviews(62 reviews)
The Sanctuary at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Boston-Modern Spacious Family Friendly Apartment w/Parking
Sleeps 5 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
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