Holiday rentals near Castle Island
We found 2,446 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:3 Oct - 10 Oct
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$12,701
NZ$12,701
NZ$1,814 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Penthouse W Roof-top
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Back-Bay Upscale Central Penthouse W Roof-top
Boston, Massachusetts
16% off
Price is NZ$9,848
NZ$9,848
NZ$1,407 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$12,701
NZ$12,701
NZ$1,814 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$15,165
NZ$15,165
NZ$2,166 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$38,878
NZ$38,878
NZ$5,554 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$10,702
NZ$10,702
NZ$1,529 per night
includes taxes & fees
Image gallery for "Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
9.89.8 out of 10 rating
Exceptional
(43 reviews)
"Travelers Choice Award" "Best of Boston" Green Turtle Houseboat Suite #2
Boston, MA
8% off
Price is NZ$5,067
NZ$5,067
NZ$724 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$7,198
NZ$7,198
NZ$1,028 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
(12 reviews)
Beautiful Oceanfront Luxurious 2 bedroom 2 story condo, mins from Boston!
Revere, MA
8% off
Price is NZ$4,708
NZ$4,708
NZ$673 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$8,803
NZ$8,803
NZ$1,258 per night
includes taxes & fees
Image gallery for Lovely Cape Cod Style Home ~ Close To Boston ~ Hot Tub ~ Steps To Walking Trails
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Lovely Cape Cod Style Home ~ Close To Boston ~ Hot Tub ~ Steps To Walking Trails
Hingham, MA
8% off
Price is NZ$15,094
NZ$15,094
NZ$2,156 per night
includes taxes & fees
Image gallery for Cody's Place Winthrop Boston Logan Airport Beaches
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Cody's Place Winthrop Boston Logan Airport Beaches
Winthrop, MA
8% off
Price is NZ$2,865
NZ$2,865
NZ$409 per night
includes taxes & fees
Image gallery for 14b-Charming, beautiful 3-bedroom apartment in Boston
9.89.8 out of 10 rating
Exceptional
(7 reviews)
14b-Charming, beautiful 3-bedroom apartment in Boston
Boston, MA
6% off
Price is NZ$6,184
NZ$6,184
NZ$883 per night
includes taxes & fees
Image gallery for Luxe & Luminous – 4BR Urban Escape
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxe & Luminous – 4BR Urban Escape
Boston, MA
7% off
Price is NZ$6,494
NZ$6,494
NZ$928 per night
includes taxes & fees
Image gallery for Contemporary Farmhouse-Style Retreat | near T
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Contemporary Farmhouse-Style Retreat | near T
Boston, Massachusetts
20% off
Price is NZ$6,837
NZ$6,837
NZ$977 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$8,601
NZ$8,601
NZ$1,229 per night
includes taxes & fees
Image gallery for Waterfront Beach Home With Attached In- Law Suite
1010 out of 10 rating
Exceptional
(33 reviews)
Waterfront Beach Home With Attached In- Law Suite
Weymouth, MA
8% off
Price is NZ$8,315
NZ$8,315
NZ$1,188 per night
includes taxes & fees
Image gallery for Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area
9.69.6 out of 10 rating
Exceptional
(142 reviews)
Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area
Boston, MA
11% off
Price is NZ$3,124
NZ$3,124
NZ$446 per night
includes taxes & fees
Image gallery for Comfortable and conveniently located.
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Comfortable and conveniently located.
Medford, MA
23% off
Price is NZ$4,376
NZ$4,376
NZ$625 per night
includes taxes & fees
Image gallery for * Beautiful condo 1st floor walk to public trans T mins to downtown Boston
9.69.6 out of 10 rating
Exceptional
(43 reviews)
* Beautiful condo 1st floor walk to public trans T mins to downtown Boston
Boston, MA
8% off
Price is NZ$7,934
NZ$7,934
NZ$1,133 per night
includes taxes & fees
Image gallery for Comfy, Stylish Apt. Near Uni's, Driveway
1010 out of 10 rating
Exceptional
(6 reviews)
Comfy, Stylish Apt. Near Uni's, Driveway
Somerville, MA
8% off
Price is NZ$5,664
NZ$5,664
NZ$809 per night
includes taxes & fees
Image gallery for 30/1 - SPRING GETAWAY 10% OFF! Fully furnished 1st floor apartment in Boston
9.29.2 out of 10 rating
Wonderful
(7 reviews)
30/1 - SPRING GETAWAY 10% OFF! Fully furnished 1st floor apartment in Boston
Boston, MA
8% off
Price is NZ$4,602
NZ$4,602
NZ$657 per night
includes taxes & fees
Image gallery for 37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
9.09.0 out of 10 rating
Wonderful
(30 reviews)
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
Quincy, MA
8% off
Price is NZ$5,088
NZ$5,088
NZ$727 per night
includes taxes & fees
Image gallery for Spacious, New Renovation | Near T
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious, New Renovation | Near T
Boston, Massachusetts
24% off
Price is NZ$10,858
NZ$10,858
NZ$1,551 per night
includes taxes & fees
Find spaces that suit your style
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Spectacular Ocean Sunsets I Pet Friendly
Sleeps 6 · 3 bedrooms · 2 bathrooms
The Pistachio Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
Pet-Friendly Revere Getaway, Steps from the T!
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
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)
558-2 3BR - Boston Renovated Nest near Aquarium
Sleeps 13 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
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