Holiday rentals near Winter Pond
We found 3,010 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: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 NZ$13,022
NZ$13,022
NZ$1,860 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$5,248
NZ$5,248
NZ$750 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$13,022
NZ$13,022
NZ$1,860 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$4,093
NZ$4,093
NZ$585 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$15,548
NZ$15,548
NZ$2,221 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$16,374
NZ$16,374
NZ$2,339 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$23,870
NZ$23,870
NZ$3,410 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$31,871
NZ$31,871
NZ$4,553 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$3,028
NZ$3,028
NZ$433 per night
includes taxes & fees
Image gallery for MAJESTIC 1800s stately home on Chestnut street. The Nathaniel West House!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
MAJESTIC 1800s stately home on Chestnut street. The Nathaniel West House!
Salem, MA
20% off
Price is NZ$15,014
NZ$15,014
NZ$2,145 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$8,923
NZ$8,923
NZ$1,275 per night
includes taxes & fees
Image gallery for Downtown Salem - Park & Play Modern 3 Bedroom
1010 out of 10 rating
Exceptional
(43 reviews)
Downtown Salem - Park & Play Modern 3 Bedroom
Salem, MA
9% off
Price is NZ$6,566
NZ$6,566
NZ$938 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 NZ$5,883
NZ$5,883
NZ$840 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 NZ$17,968
NZ$17,968
NZ$2,567 per night
includes taxes & fees
Image gallery for Stylish Studio - ✓Sanitized ✓Private ✓Spotless
1010 out of 10 rating
Exceptional
(5 reviews)
Stylish Studio - ✓Sanitized ✓Private ✓Spotless
Arlington, MA
8% off
Price is NZ$1,821
NZ$1,821
NZ$260 per night
includes taxes & fees
Image gallery for Boston-Modern Spacious Family Friendly Apartment w/Parking
1010 out of 10 rating
Exceptional
(90 reviews)
Boston-Modern Spacious Family Friendly Apartment w/Parking
Boston, MA
7% off
Price is NZ$3,385
NZ$3,385
NZ$484 per night
includes taxes & fees
Image gallery for Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA
1010 out of 10 rating
Exceptional
(62 reviews)
Historic Federal Period brick mansion on fabled Chestnut Street, Salem, MA
Salem, MA
8% off
Price is NZ$18,624
NZ$18,624
NZ$2,661 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$10,409
NZ$10,409
NZ$1,487 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
8% off
Price is NZ$11,108
NZ$11,108
NZ$1,587 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 NZ$8,880
NZ$8,880
NZ$1,269 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$3,556
NZ$3,556
NZ$508 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 NZ$9,902
NZ$9,902
NZ$1,415 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
8% off
Price is NZ$6,199
NZ$6,199
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$5,032
NZ$5,032
NZ$719 per night
includes taxes & fees
Find spaces that suit your style
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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
550 reviews(550 reviews)
No. 284 powered by Sonder
Sleeps 2 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
894 reviews(894 reviews)
Temple Place Suites
Sleeps 3 · 1 bedroom
6.86.8 out of 10
199 reviews(199 reviews)
Beautiful Retreat close to Downtown Boston. Pets friendly.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Sonder at Pierce Boston
Sleeps 6 · 3 bedrooms
9.09.0 out of 10
Wonderfulwonderful
227 reviews(227 reviews)
Premier Suites - Bay Village
Sleeps 2 · 1 bedroom
6.26.2 out of 10
150 reviews(150 reviews)
Top rated rentals - Winter Pond
Great property!
1010 out of 10
Exceptionalexceptional
69 reviews(69 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