Holiday rentals near Winter Pond
We found 3,039 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:31 Oct - 7 Nov
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(76 reviews)
Beautiful Boston Brownstone!
Boston, MA
8% off
Price is NZ$7,260
NZ$7,260
NZ$1,037 per night
includes taxes & fees
Image gallery for Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Garden Getaway 2BR Minutes to Salem, Beach, and train to Boston!
Beverly, MA
8% off
Price is NZ$5,374
NZ$5,374
NZ$768 per night
includes taxes & fees
Image gallery for NEW 2BR Historic Marblehead Home+Minutes to Beach
1010 out of 10 rating
Exceptional
(8 reviews)
NEW 2BR Historic Marblehead Home+Minutes to Beach
Marblehead, MA
8% off
Price is NZ$5,826
NZ$5,826
NZ$832 per night
includes taxes & fees
Image gallery for Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
1010 out of 10 rating
Exceptional
(64 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston, MA
8% off
Price is NZ$19,432
NZ$19,432
NZ$2,776 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
(62 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
14% off
Price is NZ$4,668
NZ$4,668
NZ$667 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Condo Bos Common Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
Back-Bay Upscale Central Condo Bos Common Downtown
Boston, Massachusetts
8% off
Price is NZ$8,897
NZ$8,897
NZ$1,271 per night
includes taxes & fees
Image gallery for Stunning South End/Back Bay Penthouse!
1010 out of 10 rating
Exceptional
(89 reviews)
Stunning South End/Back Bay Penthouse!
Boston, MA
8% off
Price is NZ$7,918
NZ$7,918
NZ$1,131 per night
includes taxes & fees
Image gallery for Back-Bay 2BR Penthouse w Roof top and GYM
8.48.4 out of 10 rating
Very good
(6 reviews)
Back-Bay 2BR Penthouse w Roof top and GYM
Boston, Massachusetts
15% off
Price is NZ$7,907
NZ$7,907
NZ$1,130 per night
includes taxes & fees
Image gallery for Lovely Studio Walk to Wellesley and Babson College
1010 out of 10 rating
Exceptional
(23 reviews)
Lovely Studio Walk to Wellesley and Babson College
Wellesley, MA
8% off
Price is NZ$3,085
NZ$3,085
NZ$441 per night
includes taxes & fees
Image gallery for 39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
9.69.6 out of 10 rating
Exceptional
(43 reviews)
39-SPRING GETAWAY EARLY BIRD 10%! Newly Built & Cozy Townhouse
Quincy, MA
8% off
Price is NZ$4,576
NZ$4,576
NZ$654 per night
includes taxes & fees
Image gallery for SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
9.69.6 out of 10 rating
Exceptional
(26 reviews)
SPRING GETAWAY EARLY BIRD 10% - 82 Newly renovated, luxury apartment in Boston
Boston, MA
8% off
Price is NZ$4,060
NZ$4,060
NZ$580 per night
includes taxes & fees
Image gallery for Enjoy Gorgeous Sunsets from Your Waterfront Beach Cottage
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Enjoy Gorgeous Sunsets from Your Waterfront Beach Cottage
Hull, MA
6% off
Price is NZ$5,130
NZ$5,130
NZ$733 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
6% off
Price is NZ$6,069
NZ$6,069
NZ$867 per night
includes taxes & fees
Image gallery for Pleasant and fully furnished 4-bedroom and two bathrooms house in Braintree MA
1010 out of 10 rating
Exceptional
(6 reviews)
Pleasant and fully furnished 4-bedroom and two bathrooms house in Braintree MA
Braintree, MA
22% off
Price is NZ$5,499
NZ$5,499
NZ$786 per night
includes taxes & fees
Image gallery for 76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
9.69.6 out of 10 rating
Exceptional
(7 reviews)
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston
Boston, MA
12% off
Price is NZ$5,758
NZ$5,758
NZ$823 per night
includes taxes & fees
Image gallery for Spacious Triplex with Large backyard FreePrkg
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Spacious Triplex with Large backyard FreePrkg
Boston, MA
8% off
Price is NZ$41,315
NZ$41,315
NZ$5,902 per night
includes taxes & fees
Image gallery for Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
8.48.4 out of 10 rating
Very good
(6 reviews)
Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
Boston, MA
8% off
Price is NZ$10,267
NZ$10,267
NZ$1,467 per night
includes taxes & fees
Image gallery for 1-Bedroom Apartment in Milton Lower Mills convenient to Boston & Cambridge
9.49.4 out of 10 rating
Exceptional
(12 reviews)
1-Bedroom Apartment in Milton Lower Mills convenient to Boston & Cambridge
Boston, MA
8% off
Price is NZ$1,963
NZ$1,963
NZ$280 per night
includes taxes & fees
Image gallery for Historic Private Auburndale Retreat Near Boston!
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Historic Private Auburndale Retreat Near Boston!
Newton, MA
7% off
Price is NZ$2,778
NZ$2,778
NZ$397 per night
includes taxes & fees
Image gallery for Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
8.68.6 out of 10 rating
Excellent
(35 reviews)
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Hull, MA
8% off
Price is NZ$2,663
NZ$2,663
NZ$380 per night
includes taxes & fees
Image gallery for 76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
1010 out of 10 rating
Exceptional
(8 reviews)
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Boston, MA
8% off
Price is NZ$7,514
NZ$7,514
NZ$1,073 per night
includes taxes & fees
Image gallery for Travelers Choice Best of Boston Houseboat Suite 2!
9.89.8 out of 10 rating
Exceptional
(43 reviews)
Travelers Choice Best of Boston Houseboat Suite 2!
Boston, MA
8% off
Price is NZ$5,208
NZ$5,208
NZ$744 per night
includes taxes & fees
Image gallery for Beautiful Dorchester Home in Boston!
1010 out of 10 rating
Exceptional
(5 reviews)
Beautiful Dorchester Home in Boston!
Boston, MA
8% off
Price is NZ$7,373
NZ$7,373
NZ$1,053 per night
includes taxes & fees
Image gallery for Great Apartment on River/ Harvard Square two blocks
8.88.8 out of 10 rating
Excellent
(16 reviews)
Great Apartment on River/ Harvard Square two blocks
Cambridge, MA
8% off
Price is NZ$2,818
NZ$2,818
NZ$403 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Pond
Showing deals for: 30 Oct - 2 Nov
Global Luxury Suites Downtown Boston
Sleeps 3 · 1 bedroom
8.08.0 out of 10
Very goodvery good
569 reviews(569 reviews)
The current price is NZ$1,794
NZ$1,794
for 3 nights, 1 room
NZ$598 per night
includes taxes & fees
Temple Place Suites
Sleeps 3 · 1 bedroom
7.07.0 out of 10
Goodgood
254 reviews(254 reviews)
The current price is NZ$1,798
NZ$1,798
for 3 nights, 1 apartment
NZ$599 per night
includes taxes & fees
Premier Suites - Bay Village
Sleeps 2 · 1 bedroom
6.26.2 out of 10
190 reviews(190 reviews)
The current price is NZ$1,495
NZ$1,495
for 3 nights, 1 room
NZ$498 per night
includes taxes & fees
Bay Village Suites
Sleeps 1 · 1 bedroom
6.46.4 out of 10
184 reviews(184 reviews)
The current price is NZ$949
NZ$949
for 3 nights, 1 room
NZ$316 per night
includes taxes & fees
Maverick Suites at 28 Fenway
Sleeps 2 · 1 bedroom
8.88.8 out of 10
Excellentexcellent
250 reviews(250 reviews)
The current price is NZ$1,571
NZ$1,571
for 3 nights, 1 apartment
NZ$524 per night
includes taxes & fees
The Sunset Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is NZ$806
NZ$806
for 3 nights, 1 room
NZ$269 per night
includes taxes & fees
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