Holiday rentals near Winthrop Park
We found 2,447 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:15 Aug - 22 Aug
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$8,173
NZ$8,173
NZ$1,168 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$13,130
NZ$13,130
NZ$1,876 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$9,184
NZ$9,184
NZ$1,312 per night
includes taxes & fees
Image gallery for Heart of Back Bay 3BR 2BA Condo
9.29.2 out of 10 rating
Wonderful
(16 reviews)
Heart of Back Bay 3BR 2BA Condo
Boston, MA
8% off
Price is NZ$21,013
NZ$21,013
NZ$3,002 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$5,292
NZ$5,292
NZ$756 per night
includes taxes & fees
Image gallery for Free Parking at 1 Bed Basement Apt, Near BU & MIT
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Free Parking at 1 Bed Basement Apt, Near BU & MIT
Boston, Massachusetts
6% off
Price is NZ$5,500
NZ$5,500
NZ$786 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$13,130
NZ$13,130
NZ$1,876 per night
includes taxes & fees
Image gallery for Modern Fenway Retreat: 2BR/2BA
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Modern Fenway Retreat: 2BR/2BA
Boston, MA
8% off
Price is NZ$13,130
NZ$13,130
NZ$1,876 per night
includes taxes & fees
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(66 reviews)
Beautiful Boston Brownstone!
Boston, MA
8% off
Price is NZ$7,843
NZ$7,843
NZ$1,120 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$4,127
NZ$4,127
NZ$590 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$15,677
NZ$15,677
NZ$2,240 per night
includes taxes & fees
Image gallery for Stunning South End/Back Bay Penthouse!
1010 out of 10 rating
Exceptional
(86 reviews)
Stunning South End/Back Bay Penthouse!
Boston, MA
8% off
Price is NZ$8,567
NZ$8,567
NZ$1,224 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$3,053
NZ$3,053
NZ$436 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$40,190
NZ$40,190
NZ$5,741 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$7,981
NZ$7,981
NZ$1,140 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
6% off
Price is NZ$3,757
NZ$3,757
NZ$537 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$32,134
NZ$32,134
NZ$4,591 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$8,997
NZ$8,997
NZ$1,285 per night
includes taxes & fees
Image gallery for Renovated Beach House Close to Everything, Minutes to Boston
9.49.4 out of 10 rating
Exceptional
(94 reviews)
Renovated Beach House Close to Everything, Minutes to Boston
Quincy, MA
8% off
Price is NZ$4,543
NZ$4,543
NZ$649 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$10,495
NZ$10,495
NZ$1,499 per night
includes taxes & fees
Image gallery for Unique Cathedral Ceiling Condo W/D, Parking
1010 out of 10 rating
Exceptional
(7 reviews)
Unique Cathedral Ceiling Condo W/D, Parking
Arlington, MA
8% off
Price is NZ$3,749
NZ$3,749
NZ$536 per night
includes taxes & fees
Image gallery for Modern, Spacious, bright, private apartment
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Modern, Spacious, bright, private apartment
Watertown, MA
8% off
Price is NZ$2,358
NZ$2,358
NZ$337 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 NZ$2,842
NZ$2,842
NZ$406 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$5,073
NZ$5,073
NZ$725 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winthrop Park
Victorian home
Sleeps 8 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
4BR Boston Home 5 minutes walk to Subway
Sleeps 12 · 4 bedrooms · 2 bathrooms
5BR3B Lux Home Walk to Subway Near Downtown
Sleeps 14 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
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