Vacation rentals near Monument Square
We found 2,631 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Monument Square, scroll through and discover private vacation rentals to find the perfect one for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Monument Square
Showing deals for:Nov 7 - Nov 14
Image gallery for Exquisite North End 1brm
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Exquisite North End 1brm
Boston, MA
5% off
Price is CA $342
CA $342
CA $3,218 total
CA $3,218 total
includes taxes & fees
Image gallery for Perfect North End Studio
9.49.4 out of 10 rating
Exceptional
(32 reviews)
Perfect North End Studio
Boston, MA
5% off
Price is CA $304
CA $304
CA $2,875 total
CA $2,875 total
includes taxes & fees
Image gallery for Beautiful Boston Brownstone!
1010 out of 10 rating
Exceptional
(77 reviews)
Beautiful Boston Brownstone!
Boston, MA
10% off
Price is CA $619
CA $619
CA $5,678 total
CA $5,678 total
includes taxes & fees
Image gallery for Spacious vacation townhome unit with a pool
1010 out of 10 rating
Exceptional
(12 reviews)
Spacious vacation townhome unit with a pool
Weston, MA
10% off
Price is CA $417
CA $417
CA $3,608 total
CA $3,608 total
includes taxes & fees
Image gallery for 80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
9.49.4 out of 10 rating
Exceptional
(15 reviews)
80/2 - SPRING GETAWAY EARLY BIRD 10%! Brand new modern and comfortable apartment
Boston, MA
19% off
Price is CA $365
CA $365
CA $3,466 total
CA $3,466 total
includes taxes & fees
Image gallery for Central Boston Beacon Hill 2brm
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Central Boston Beacon Hill 2brm
Boston, MA
5% off
Price is CA $466
CA $466
CA $4,343 total
CA $4,343 total
includes taxes & fees
Image gallery for Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
1010 out of 10 rating
Exceptional
(65 reviews)
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Boston, MA
10% off
Price is CA $1,831
CA $1,831
CA $16,153 total
CA $16,153 total
includes taxes & fees
Image gallery for Modern 2BR/ Close to Boston with a lovely outdoor space
9.49.4 out of 10 rating
Exceptional
(22 reviews)
Modern 2BR/ Close to Boston with a lovely outdoor space
Melrose, MA
10% off
Price is CA $308
CA $308
CA $2,900 total
CA $2,900 total
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
(63 reviews)
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Boston, MA
19% off
Price is CA $390
CA $390
CA $3,786 total
CA $3,786 total
includes taxes & fees
Image gallery for Lux 2nd floor 3brm/1bath
1010 out of 10 rating
Exceptional
(5 reviews)
Lux 2nd floor 3brm/1bath
Boston, MA
5% off
Price is CA $725
CA $725
CA $6,734 total
CA $6,734 total
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, MA
10% off
Price is CA $721
CA $721
CA $7,062 total
CA $7,062 total
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, MA
20% off
Price is CA $640
CA $640
CA $6,256 total
CA $6,256 total
includes taxes & fees
Image gallery for The Hive: A Honeybee-Themed Retreat. Wi-fi, Video Games, EV Charger, Garden View
1010 out of 10 rating
Exceptional
(10 reviews)
The Hive: A Honeybee-Themed Retreat. Wi-fi, Video Games, EV Charger, Garden View
Billerica, MA
24% off
Price is CA $194
CA $194
CA $1,755 total
CA $1,755 total
includes taxes & fees
Image gallery for New 5B3B Single Family with Central AC
9.89.8 out of 10 rating
Exceptional
(28 reviews)
New 5B3B Single Family with Central AC
Arlington, MA
5% off
Price is CA $736
CA $736
CA $6,755 total
CA $6,755 total
includes taxes & fees
Image gallery for Sunny Dog Friendly Union Sq 1brm
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Sunny Dog Friendly Union Sq 1brm
Somerville, MA
5% off
Price is CA $258
CA $258
CA $2,414 total
CA $2,414 total
includes taxes & fees
Image gallery for 4BR, 4Bath Dream Home Experience: sauna, hot tub, pool. Explore Boston in Style!
9.49.4 out of 10 rating
Exceptional
(22 reviews)
4BR, 4Bath Dream Home Experience: sauna, hot tub, pool. Explore Boston in Style!
Newton, MA
10% off
Price is CA $742
CA $742
CA $6,808 total
CA $6,808 total
includes taxes & fees
Image gallery for Historic Townhouse in the Heart of Boston
9.49.4 out of 10 rating
Exceptional
(36 reviews)
Historic Townhouse in the Heart of Boston
Boston, MA
5% off
Price is CA $783
CA $783
CA $7,246 total
CA $7,246 total
includes taxes & fees
Image gallery for Luxury apartment seaport
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Luxury apartment seaport
Boston, MA
10% off
Price is CA $494
CA $494
CA $4,706 total
CA $4,706 total
includes taxes & fees
Image gallery for Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Medford, MA
19% off
Price is CA $231
CA $231
CA $2,228 total
CA $2,228 total
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
10% off
Price is CA $681
CA $681
CA $6,228 total
CA $6,228 total
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
19% off
Price is CA $309
CA $309
CA $2,978 total
CA $2,978 total
includes taxes & fees
Image gallery for 14b-Charming, beautiful 3-bedroom apartment in Boston
9.89.8 out of 10 rating
Exceptional
(8 reviews)
14b-Charming, beautiful 3-bedroom apartment in Boston
Boston, MA
10% off
Price is CA $427
CA $427
CA $4,023 total
CA $4,023 total
includes taxes & fees
Image gallery for Lovely Studio Walk to Wellesley and Babson College
1010 out of 10 rating
Exceptional
(24 reviews)
Lovely Studio Walk to Wellesley and Babson College
Wellesley, MA
10% off
Price is CA $277
CA $277
CA $2,491 total
CA $2,491 total
includes taxes & fees
Image gallery for Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Boston, MA
5% off
Price is CA $868
CA $868
CA $7,912 total
CA $7,912 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Monument Square
Global Luxury Suites Downtown Boston
Sleeps 3 · 1 bedroom
8.08.0 out of 10
Very goodvery good
572 reviews(572 reviews)
Temple Place Suites
Sleeps 3 · 1 bedroom
7.07.0 out of 10
Goodgood
257 reviews(257 reviews)
Premier Suites - Bay Village
Sleeps 2 · 1 bedroom
6.26.2 out of 10
198 reviews(198 reviews)
Bay Village Suites
Sleeps 1 · 1 bedroom
6.46.4 out of 10
189 reviews(189 reviews)
Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay
Sleeps 2 · 1 bathroom
8.88.8 out of 10
Excellentexcellent
68 reviews(68 reviews)
Take An Amazing Vacation! Pet-Friendly Property, Near Liberty Ride Trolley Tour!
Sleeps 4 · 1 bedroom · 1 bathroom
7.47.4 out of 10
Goodgood
13 reviews(13 reviews)
Top rated rentals - Monument Square
Nice trip
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Nice accomodation. Near Downtown Boston. The hote gives us a lot of tips of what to do.
karine R.
Stayed May 2025
Excellent
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
My family and I truly enjoyed our stay at the Ashmont suite, the house was clean and beautiful just as shown in the pictures.
Eddie was really helpful and answered all our questions. I really recommend this host for anyone looking for a place to stay while visiting Boston.
benedicte v.
Stayed Jul 2024
Amazing host.
1010 out of 10
Exceptionalexceptional
229 reviews(229 reviews)
Definitely going back and will definitely stay at the Green Turtle. Thank you so much Karen and Jon for making my 55th Birthday one I will never forget…
Cherryl B.
Stayed Aug 2023
Beautiful property in great location!
1010 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
This apartment was the perfect fit for our party of six. Peter was amazing to deal with, very responsive and helpful! Thanks for making our stay memorable!
Cheryl S.
Stayed Apr 2023
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, yards and more
More for lessMore space, more privacy, more amenities — more value