Holiday rentals near Castle Island
We found 2,413 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals near Castle Island that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for spending time at your holiday home, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Castle Island
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$7,835
NZ$7,835
NZ$1,119 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 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 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 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 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$7,652
NZ$7,652
NZ$1,093 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 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
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 Spacious Triplex with Large outdoor space FreePrkg
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious Triplex with Large outdoor space FreePrkg
Boston, MA
8% off
Price is NZ$39,580
NZ$39,580
NZ$5,654 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 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 Boston-Modern Spacious Family Friendly Apartment w/Parking
1010 out of 10 rating
Exceptional
(90 reviews)
Boston-Modern Spacious Family Friendly Apartment w/Parking
Boston, MA
7% off
Price is NZ$3,320
NZ$3,320
NZ$474 per night
includes taxes & fees
Image gallery for View the Boston Marathon at mile 23, minutes from this 4 bedroom, 4 bath home
9.49.4 out of 10 rating
Exceptional
(12 reviews)
View the Boston Marathon at mile 23, minutes from this 4 bedroom, 4 bath home
Brookline, MA
8% off
Price is NZ$8,818
NZ$8,818
NZ$1,260 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
8% off
Price is NZ$10,336
NZ$10,336
NZ$1,477 per night
includes taxes & fees
Image gallery for Spacious 4 Bed / 2.5 Bath Condo with Large Kitchen, Free Parking - Pet Friendly!
1010 out of 10 rating
Exceptional
(18 reviews)
Spacious 4 Bed / 2.5 Bath Condo with Large Kitchen, Free Parking - Pet Friendly!
Boston, MA
8% off
Price is NZ$11,029
NZ$11,029
NZ$1,576 per night
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
8.88.8 out of 10 rating
Excellent
(8 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
8% off
Price is NZ$6,540
NZ$6,540
NZ$934 per night
includes taxes & fees
Image gallery for Private Luxury House, Fenced Yard, Short Walk to Harvard/MIT/T. Dogs OK.
9.89.8 out of 10 rating
Exceptional
(114 reviews)
Private Luxury House, Fenced Yard, Short Walk to Harvard/MIT/T. Dogs OK.
Cambridge, MA
8% off
Price is NZ$7,631
NZ$7,631
NZ$1,090 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$4,996
NZ$4,996
NZ$714 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Castle Island
3 Bed 2 Bath Direct Ocean View Beach Condo
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.28.2 out of 10
Very goodvery good
25 reviews(25 reviews)
New Built XL Modern House Near Tenean Beach,UMass Boston,Highway. With EVCharger
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
3-bedroom luxury townhome in charming Boston with WiFi, AC and private parking
Sleeps 8 · 3 bedrooms · 2 bathrooms
Direct ocean view 4-bed 2 bath in fabulous Hull with AC,WiFi deck walk to beach
Sleeps 8 · 4 bedrooms · 2 bathrooms
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Red Door Oasis 5mins to Boston
Sleeps 12 · 6 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
Top rated rentals - Castle Island
Great property!
1010 out of 10
Exceptionalexceptional
69 reviews(69 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