Holiday rentals near Winter Pond
We found 3,014 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals close to Winter Pond that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Winter Pond
Showing deals for:18 Jul - 25 Jul
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$13,034
NZ$13,034
NZ$1,862 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$13,034
NZ$13,034
NZ$1,862 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$15,563
NZ$15,563
NZ$2,223 per night
includes taxes & fees
Image gallery for The Witch Den - Trendy and Historical Home in the heart of Salem
1010 out of 10 rating
Exceptional
(13 reviews)
The Witch Den - Trendy and Historical Home in the heart of Salem
Salem, MA
8% off
Price is NZ$16,389
NZ$16,389
NZ$2,341 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 NZ$7,018
NZ$7,018
NZ$1,003 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$39,898
NZ$39,898
NZ$5,700 per night
includes taxes & fees
Image gallery for Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.
1010 out of 10 rating
Exceptional
(23 reviews)
Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.
Walpole, MA
8% off
Price is NZ$23,893
NZ$23,893
NZ$3,413 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$31,901
NZ$31,901
NZ$4,557 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$3,031
NZ$3,031
NZ$433 per night
includes taxes & fees
Image gallery for Luxurious 4 bed 2 bath in the city of Somerville/Cambridge|2min from GreenLine
1010 out of 10 rating
Exceptional
(21 reviews)
Luxurious 4 bed 2 bath in the city of Somerville/Cambridge|2min from GreenLine
Somerville, MA
12% off
Price is NZ$6,405
NZ$6,405
NZ$915 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
(123 reviews)
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
Boston, MA
8% off
Price is NZ$8,931
NZ$8,931
NZ$1,276 per night
includes taxes & fees
Image gallery for Stunning beautiful and gorgeous home near Boston!
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Stunning beautiful and gorgeous home near Boston!
Quincy, MA
11% off
Price is NZ$6,131
NZ$6,131
NZ$876 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 NZ$3,520
NZ$3,520
NZ$503 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
8% off
Price is NZ$10,419
NZ$10,419
NZ$1,488 per night
includes taxes & fees
Image gallery for Lovely Downtown Beverly
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Lovely Downtown Beverly
Beverly, MA
8% off
Price is NZ$4,108
NZ$4,108
NZ$587 per night
includes taxes & fees
Image gallery for Large 4 Bedroom apartments, 3RD FL Brighton
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Large 4 Bedroom apartments, 3RD FL Brighton
Boston, MA
8% off
Price is NZ$6,205
NZ$6,205
NZ$886 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 NZ$5,036
NZ$5,036
NZ$719 per night
includes taxes & fees
Image gallery for Historic 1686 Home Near Downtown l 5BR Retreat
1010 out of 10 rating
Exceptional
(5 reviews)
Historic 1686 Home Near Downtown l 5BR Retreat
Beverly, MA
8% off
Price is NZ$9,790
NZ$9,790
NZ$1,399 per night
includes taxes & fees
Image gallery for Mid Century in historic Lexington
1010 out of 10 rating
Exceptional
(48 reviews)
Mid Century in historic Lexington
Lexington, MA
8% off
Price is NZ$4,162
NZ$4,162
NZ$595 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 NZ$5,325
NZ$5,325
NZ$761 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 NZ$6,243
NZ$6,243
NZ$892 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
(65 reviews)
Harvard House Host Your 2025 Family Gathering In Boston at This Beautiful Venue
Waltham, MA
8% off
Price is NZ$11,286
NZ$11,286
NZ$1,612 per night
includes taxes & fees
Image gallery for Spacious vacation townhome unit with a pool
1010 out of 10 rating
Exceptional
(10 reviews)
Spacious vacation townhome unit with a pool
Weston, MA
6% off
Price is NZ$5,080
NZ$5,080
NZ$726 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 NZ$9,034
NZ$9,034
NZ$1,291 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Winter Pond
Global Luxury Suites Downtown Boston
Sleeps 3 · 1 bedroom
8.08.0 out of 10
Very goodvery good
545 reviews(545 reviews)
No. 284 powered by Sonder
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
888 reviews(888 reviews)
Temple Place Suites
Sleeps 3 · 1 bedroom
6.86.8 out of 10
197 reviews(197 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
216 reviews(216 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