Holiday rentals near Winthrop Park
We found 2,483 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals close to Winthrop Park that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, including Wi-Fi and parking. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Winthrop Park
Showing deals for:25 Jul - 1 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 £5,802
£5,802
£829 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 £2,101
£2,101
£300 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 £5,848
£5,848
£835 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 £6,977
£6,977
£997 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 £14,149
£14,149
£2,021 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
8% off
Price is £3,249
£3,249
£464 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 £1,389
£1,389
£198 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 £4,043
£4,043
£578 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 £1,545
£1,545
£221 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 £4,134
£4,134
£591 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 £3,052
£3,052
£436 per night
includes taxes & fees
Image gallery for Located north of Boston/ comfort and relaxation in your home away from home
1010 out of 10 rating
Exceptional
(33 reviews)
Located north of Boston/ comfort and relaxation in your home away from home
Woburn, MA
8% off
Price is £1,324
£1,324
£189 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 £4,863
£4,863
£695 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 £17,516
£17,516
£2,502 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 £3,700
£3,700
£529 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 £2,280
£2,280
£326 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 £2,852
£2,852
£407 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 £2,672
£2,672
£382 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 £7,059
£7,059
£1,008 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 £2,448
£2,448
£350 per night
includes taxes & fees
Image gallery for Harvard House Host Your 2025 Family Gathering In Boston at This Beautiful Venue
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Harvard House Host Your 2025 Family Gathering In Boston at This Beautiful Venue
Waltham, MA
8% off
Price is £5,266
£5,266
£752 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
(54 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
7% off
Price is £3,093
£3,093
£442 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 £4,095
£4,095
£585 per night
includes taxes & fees
Image gallery for Leafy & Tranquil, Artist House
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Leafy & Tranquil, Artist House
Boston, MA
7% off
Price is £2,060
£2,060
£294 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winthrop Park
Global Luxury Suites Downtown Boston
Sleeps 3 · 1 bedroom
8.08.0 out of 10
Very goodvery good
549 reviews(549 reviews)
No. 284 powered by Sonder
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
893 reviews(893 reviews)
Temple Place Suites
Sleeps 3 · 1 bedroom
6.86.8 out of 10
198 reviews(198 reviews)
Beautiful Retreat close to Downtown Boston. Pets friendly.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
119 reviews(119 reviews)
Sonder at Pierce Boston
Sleeps 6 · 3 bedrooms
8.88.8 out of 10
Excellentexcellent
225 reviews(225 reviews)
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
Sleeps 2 · 1 bathroom
1010 out of 10
Exceptionalexceptional
219 reviews(219 reviews)
Top rated rentals - Winthrop Park
A wonderful apartment
1010 out of 10
Exceptionalexceptional
157 reviews(157 reviews)
Great Place
1010 out of 10
Exceptionalexceptional
256 reviews(256 reviews)
Lovely family home
1010 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
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