Holiday rentals near Castle Island
We found 2,427 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:1 Aug - 8 Aug
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 £5,750
£5,750
£821 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 £2,367
£2,367
£338 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
7% off
Price is £5,795
£5,795
£828 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 £6,914
£6,914
£988 per night
includes taxes & fees
Image gallery for Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
1010 out of 10 rating
Exceptional
(69 reviews)
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Quincy, MA
8% off
Price is £7,977
£7,977
£1,140 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 £14,021
£14,021
£2,003 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 £2,682
£2,682
£383 per night
includes taxes & fees
Image gallery for extended stays
9.69.6 out of 10 rating
Exceptional
(24 reviews)
extended stays
Boston, MA
7% off
Price is £1,377
£1,377
£197 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 £4,007
£4,007
£572 per night
includes taxes & fees
Image gallery for Boston-Modern Spacious Family Friendly Apartment w/Parking
1010 out of 10 rating
Exceptional
(89 reviews)
Boston-Modern Spacious Family Friendly Apartment w/Parking
Boston, MA
7% off
Price is £1,523
£1,523
£218 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
7% off
Price is £5,189
£5,189
£741 per night
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
9.89.8 out of 10 rating
Exceptional
(7 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
7% off
Price is £3,024
£3,024
£432 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 £4,096
£4,096
£585 per night
includes taxes & fees
Image gallery for Sunny 2 bedroom in Southie
1010 out of 10 rating
Exceptional
(5 reviews)
Sunny 2 bedroom in Southie
Boston, MA
7% off
Price is £4,819
£4,819
£688 per night
includes taxes & fees
Image gallery for 5BR triple decker apartment – 15 mins to City
8.68.6 out of 10 rating
Excellent
(17 reviews)
5BR triple decker apartment – 15 mins to City
Boston, MA
7% off
Price is £4,719
£4,719
£674 per night
includes taxes & fees
Image gallery for A beautiful 3BR Apartment near Harvard and MIT
9.69.6 out of 10 rating
Exceptional
(39 reviews)
A beautiful 3BR Apartment near Harvard and MIT
Cambridge, MA
8% off
Price is £2,259
£2,259
£323 per night
includes taxes & fees
Image gallery for Large 4 Bedroom apartments, 3RD FL Brighton
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Large 4 Bedroom apartments, 3RD FL Brighton
Boston, MA
7% off
Price is £2,808
£2,808
£401 per night
includes taxes & fees
Image gallery for Lovely 3 bedroom 2 bath “6 miles from downtown”
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Lovely 3 bedroom 2 bath “6 miles from downtown”
Boston, MA
7% off
Price is £2,826
£2,826
£404 per night
includes taxes & fees
Image gallery for Perfect for large group 10 beds• 4.6 mi to Downtown •steps to T 5BD/2Bth
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Perfect for large group 10 beds• 4.6 mi to Downtown •steps to T 5BD/2Bth
Boston, MA
8% off
Price is £4,563
£4,563
£652 per night
includes taxes & fees
Image gallery for Newly Renovated 4BR1BA Apartment
1010 out of 10 rating
Exceptional
(5 reviews)
Newly Renovated 4BR1BA Apartment
Boston, MA
7% off
Price is £2,648
£2,648
£378 per night
includes taxes & fees
Image gallery for Milton Retreat, 5 min to Boston ,major highways . Safe family neighborhood . 😀
9.89.8 out of 10 rating
Exceptional
(46 reviews)
Milton Retreat, 5 min to Boston ,major highways . Safe family neighborhood . 😀
Milton, MA
8% off
Price is £2,426
£2,426
£347 per night
includes taxes & fees
Image gallery for Heart of Southie - Hot Tub + Walk to Top Bars
1010 out of 10 rating
Exceptional
(11 reviews)
Heart of Southie - Hot Tub + Walk to Top Bars
Boston, Massachusetts
16% off
Price is £6,661
£6,661
£952 per night
includes taxes & fees
Image gallery for Cozy Apartment | Near T
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Cozy Apartment | Near T
Boston, Massachusetts
19% off
Price is £2,368
£2,368
£338 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
(36 reviews)
A Cozy 5BR Apartment near Harvard Square and MIT
Cambridge, MA
8% off
Price is £4,058
£4,058
£580 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Castle Island
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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)
Super Family Friendly, Private Apt Sleeps 5 -- Close to Boston & Salem MA!
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches
Sleeps 4 · 1 bedroom · 1 bathroom
Eclectic 1BR, 10 min-Boston,Near Public Transport<br>
Sleeps 4 · 1 bedroom · 1 bathroom
6.06.0 out of 10
1 review(1 review)
Modern Beachside Space - Near Boston/Airport/Train
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Top rated rentals - Castle Island
Great location
1010 out of 10
Exceptionalexceptional
104 reviews(104 reviews)
Perfect property for city break
1010 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
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