Boston holiday homes
We found 4,545 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Boston, MA (BOS-All Airports)
Showing deals for:8 Aug - 15 Aug
Image gallery for Back-Bay 2BR Penthouse w Roof top and GYM
8.48.4 out of 10 rating
Very good
(5 reviews)
Back-Bay 2BR Penthouse w Roof top and GYM
Boston, Massachusetts
15% off
Price is NZ$7,342
NZ$7,342
NZ$1,049 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Penthouse W Roof-top
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Back-Bay Upscale Central Penthouse W Roof-top
Boston, Massachusetts
15% off
Price is NZ$7,734
NZ$7,734
NZ$1,105 per night
includes taxes & fees
Image gallery for Historic Townhouse in the Heart of Boston
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Historic Townhouse in the Heart of Boston
Boston, MA
8% off
Price is NZ$9,025
NZ$9,025
NZ$1,289 per night
includes taxes & fees
Image gallery for Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum
9.49.4 out of 10 rating
Exceptional
(29 reviews)
Elegant Back Bay Brownstone - Comm Ave - 1+ Bed - One Week Minimum
Boston, MA
8% off
Price is NZ$5,211
NZ$5,211
NZ$744 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$12,930
NZ$12,930
NZ$1,847 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$12,930
NZ$12,930
NZ$1,847 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
(5 reviews)
Cozy 1-bedroom in 2-bedroom apartment in welcoming Boston with WiFi, AC
Boston, MA
12% off
Price is NZ$4,065
NZ$4,065
NZ$581 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$15,439
NZ$15,439
NZ$2,206 per night
includes taxes & fees
Image gallery for Cozy 1 Bedroom Apartment in Historic BeaconHill
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Cozy 1 Bedroom Apartment in Historic BeaconHill
Boston, MA
8% off
Price is NZ$3,547
NZ$3,547
NZ$507 per night
includes taxes & fees
Image gallery for The Witch Den - Trendy and Historical Home in the heart of Salem
1010 out of 10 rating
Exceptional
(13 reviews)
The Witch Den - Trendy and Historical Home in the heart of Salem
Salem, MA
8% off
Price is NZ$16,259
NZ$16,259
NZ$2,323 per night
includes taxes & fees
Image gallery for Hampton Beach is calling. Sleeps 10! Coastal cottage walk to everything!
1010 out of 10 rating
Exceptional
(7 reviews)
Hampton Beach is calling. Sleeps 10! Coastal cottage walk to everything!
Hampton, NH
8% off
Price is NZ$6,198
NZ$6,198
NZ$885 per night
includes taxes & fees
Image gallery for Gorgeous High End Charlestown Home - Minutes From Downtown And All Of Boston!
1010 out of 10 rating
Exceptional
(28 reviews)
Gorgeous High End Charlestown Home - Minutes From Downtown And All Of Boston!
Boston, MA
9% off
Price is NZ$7,327
NZ$7,327
NZ$1,047 per night
includes taxes & fees
Image gallery for extended stays
9.69.6 out of 10 rating
Exceptional
(24 reviews)
extended stays
Boston, MA
8% off
Price is NZ$3,007
NZ$3,007
NZ$430 per night
includes taxes & fees
Image gallery for C by the Sea - Ocean View Penthouse
1010 out of 10 rating
Exceptional
(5 reviews)
C by the Sea - Ocean View Penthouse
Gloucester, MA
8% off
Price is NZ$6,444
NZ$6,444
NZ$921 per night
includes taxes & fees
Image gallery for House near down town Salem
9.89.8 out of 10 rating
Exceptional
(40 reviews)
House near down town Salem
Salem, MA
8% off
Price is NZ$4,081
NZ$4,081
NZ$583 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$1,762
NZ$1,762
NZ$252 per night
includes taxes & fees
Image gallery for Gorgeous house walk to Harv., Tufts,; MIT. Discounts for 2 wks or more.
1010 out of 10 rating
Exceptional
(6 reviews)
Gorgeous house walk to Harv., Tufts,; MIT. Discounts for 2 wks or more.
Cambridge, MA
8% off
Price is NZ$5,901
NZ$5,901
NZ$843 per night
includes taxes & fees
Image gallery for MAJESTIC 1800s stately home on Chestnut street. The Nathaniel West House!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
MAJESTIC 1800s stately home on Chestnut street. The Nathaniel West House!
Salem, MA
20% off
Price is NZ$14,908
NZ$14,908
NZ$2,130 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
(64 reviews)
Grand piano Apt near T station towards downtown Boston, TD Garden and Hospitals.
Medford, MA
5% off
Price is NZ$3,739
NZ$3,739
NZ$534 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
(60 reviews)
Spacious & Comfy 2BR/2Bath Yacht - Heat & AC - On Freedom Trail-Walk to Downtown
Boston, MA
8% off
Price is NZ$7,720
NZ$7,720
NZ$1,103 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
(124 reviews)
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
Boston, MA
8% off
Price is NZ$8,860
NZ$8,860
NZ$1,266 per night
includes taxes & fees
Image gallery for Cute cottage by the sea - longer term winter rates available - please inquire
9.69.6 out of 10 rating
Exceptional
(75 reviews)
Cute cottage by the sea - longer term winter rates available - please inquire
Newbury, MA
8% off
Price is NZ$3,529
NZ$3,529
NZ$504 per night
includes taxes & fees
Image gallery for lovely 2-bedroom apartment with pool 2C
8.48.4 out of 10 rating
Very good
(5 reviews)
lovely 2-bedroom apartment with pool 2C
Hampton, NH
8% off
Price is NZ$6,749
NZ$6,749
NZ$964 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$31,647
NZ$31,647
NZ$4,521 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Boston
Beautiful private studio. private entrance and parking thank you, place to work,
Sleeps 2 · 1 bedroom · 1 bathroom
Riverview charming apt near beach
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Take An Amazing Vacation! Pet-Friendly Property, Near Liberty Ride Trolley Tour!
Sleeps 4 · 1 bedroom · 1 bathroom
7.47.4 out of 10
Goodgood
11 reviews(11 reviews)
JACARANDA. A comfortable, secure two-story colonial. Whole house.
Sleeps 6 · 3 bedrooms · 1+ bathroom
8.48.4 out of 10
Very goodvery good
36 reviews(36 reviews)
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
70 reviews(70 reviews)
Lovely 2 bedroom condo 5 mins from downtown
Sleeps 4 · 2 bedrooms · 3 bathrooms
5.05.0 out of 10
2 reviews(2 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value