Holiday rentals near The Wayside
We found 2,653 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's near The Wayside. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a TV. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - The Wayside
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$12,897
NZ$12,897
NZ$1,842 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$5,198
NZ$5,198
NZ$743 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$12,897
NZ$12,897
NZ$1,842 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$15,399
NZ$15,399
NZ$2,200 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$23,642
NZ$23,642
NZ$3,377 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$31,566
NZ$31,566
NZ$4,509 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$2,999
NZ$2,999
NZ$428 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$8,838
NZ$8,838
NZ$1,263 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$5,827
NZ$5,827
NZ$832 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$39,479
NZ$39,479
NZ$5,640 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$1,804
NZ$1,804
NZ$258 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$10,310
NZ$10,310
NZ$1,473 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$3,354
NZ$3,354
NZ$479 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
8% off
Price is NZ$6,523
NZ$6,523
NZ$932 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$11,001
NZ$11,001
NZ$1,572 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$8,795
NZ$8,795
NZ$1,256 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$3,479
NZ$3,479
NZ$497 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$9,808
NZ$9,808
NZ$1,401 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$4,983
NZ$4,983
NZ$712 per night
includes taxes & fees
Image gallery for Large 4 Bedroom apartments, 3RD FL Brighton
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Large 4 Bedroom apartments, 3RD FL Brighton
Boston, MA
8% off
Price is NZ$6,139
NZ$6,139
NZ$877 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$6,177
NZ$6,177
NZ$882 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
8% off
Price is NZ$10,085
NZ$10,085
NZ$1,441 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
8% off
Price is NZ$5,754
NZ$5,754
NZ$822 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$5,269
NZ$5,269
NZ$753 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Wayside
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
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)
Premier Suites - Bay Village
Sleeps 2 · 1 bedroom
6.26.2 out of 10
150 reviews(150 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