Global Luxury Suites Downtown Boston 
Best Price Match
7.9 (745 Reviews) Apartment
Apartments • Private parking • Pet friendly
Best Price Match 428+ Vacation Rentals Near Dewey Square
NearbyHoliday - Vacation Rentals in Dewey Square
Private Rooms, Shared Bath in a Private Home Minutes From Logan Airport Best Price Match
8.8 (732 Reviews) Homestay
Free WiFi • Non-smoking rooms • Family rooms
Boston East Boston • In Dewey Square · 3.8km to center
Best Price Match 
NEW! Boston Entire House Near MBTA, 3 Mi to Fenway! Best Price Match
7.8 (6 Reviews) Apartment
The entire place is yours • 307 m² size • Balcony
Best Price Match 
The Monty Boston Best Price Match
9.0 (114 Reviews) Apartment
Apartments • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 639m to center
Best Price Match 
Location+Comfort+Convenience Best Price Match
8.9 (63 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Boston East Boston • In Dewey Square · 2.2km to center
Best Price Match 
Stylish Studio the Fenway Neighborhood - Unit #106 Best Price Match
8.2 (62 Reviews) Apartment
The entire place is yours • 14 m² size • Kitchen
Best Price Match 
Harmony Medical Suites ChinaTown Best Price Match
8.3 (58 Reviews) Apartment
Apartments • Private parking • Pet friendly
Best Price Match 
Boston Monadnock Properties Best Price Match
8.6 (315 Reviews) Homestay
Free WiFi • Non-smoking rooms • Family rooms
Boston Dorchester • In Dewey Square · 4.0km to center
Best Price Match Luxury Places to Stay in Dewey Square
Over 145+ Luxury Places to Stay in or Near Dewey Square
Four Seasons Boston Best Price Match
9.1 (89 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Boston Boston Common • In Dewey Square · 1.1km to center
Best Price Match 
Boston Harbor Hotel Best Price Match
9.0 (162 Reviews) Hotel
1. Off-site parking • Indoor swimming pool • Restaurant
Best Price Match 
Four Seasons Hotel One Dalton Street, Boston Best Price Match
9.3 (170 Reviews) Hotel
Private parking • Indoor swimming pool • 3 restaurants
Best Price Match 
Mandarin Oriental, Boston Best Price Match
8.8 (51 Reviews) Hotel
Breakfast • On-site parking • Restaurant
Best Price Match 
The Ritz-Carlton, Boston Best Price Match
8.5 (43 Reviews) Hotel
Breakfast • Private parking • Restaurant
Boston Downtown Boston • In Dewey Square · 638m to center
Best Price Match 
The Newbury Boston Best Price Match
9.0 (553 Reviews) Hotel
Breakfast • 2 restaurants • Pet friendly
Best Price Match 
The Langham, Boston Best Price Match
9.2 (636 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Boston Downtown Boston • In Dewey Square · 374m to center
Best Price Match Pet-Friendly Vacation Rentals in Dewey Square
Over 172+ Pet-Friendly Vacation Rentals in or Near Dewey Square
Seaport Hotel® Boston Pets allowed Best Price Match
9.1 (2786 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Boston South Boston • In Dewey Square · 1.3km to center
Best Price Match 
Club Quarters Hotel Faneuil Hall, Boston Pets allowed Best Price Match
8.4 (4031 Reviews) Hotel
Breakfast • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 405m to center
Best Price Match The Newbury Boston Pets allowed Best Price Match
9.0 (553 Reviews) Hotel
Breakfast • 2 restaurants • Pet friendly
Best Price Match 
The Verb Hotel Pets allowed Best Price Match
9.3 (2738 Reviews) Hotel
Breakfast • Private parking • Outdoor swimming pool
Best Price Match 
The Eliot Hotel Pets allowed Best Price Match
9.1 (1508 Reviews) Hotel
Breakfast • Restaurant • Pet friendly
Best Price Match 
The Dagny Boston Pets allowed Best Price Match
9.0 (2262 Reviews) Hotel
2 restaurants • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 502m to center
Best Price Match 
The Godfrey Hotel Boston Pets allowed Best Price Match
9.0 (3506 Reviews) Hotel
Private parking • 2 restaurants • Pet friendly
Boston Downtown Boston • In Dewey Square · 526m to center
Best Price Match 
The Whitney Hotel Boston Pets allowed Best Price Match
9.1 (1062 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Boston Beacon Hill • In Dewey Square · 1.6km to center
Best Price Match Vacation Rentals in Dewey Square
Over 278+ Vacation Rentals in or Near Dewey Square
Global Luxury Suites Downtown Boston Best Price Match
7.9 (745 Reviews) Apartment
Apartments • Private parking • Pet friendly
Best Price Match Private Rooms, Shared Bath in a Private Home Minutes From Logan Airport Best Price Match
8.8 (732 Reviews) Homestay
Free WiFi • Non-smoking rooms • Family rooms
Boston East Boston • In Dewey Square · 3.8km to center
Best Price Match NEW! Boston Entire House Near MBTA, 3 Mi to Fenway! Best Price Match
7.8 (6 Reviews) Apartment
The entire place is yours • 307 m² size • Balcony
Best Price Match The Monty Boston Best Price Match
9.0 (114 Reviews) Apartment
Apartments • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 639m to center
Best Price Match Location+Comfort+Convenience Best Price Match
8.9 (63 Reviews) Apartment
The entire place is yours • 111 m² size • Free WiFi
Boston East Boston • In Dewey Square · 2.2km to center
Best Price Match Stylish Studio the Fenway Neighborhood - Unit #106 Best Price Match
8.2 (62 Reviews) Apartment
The entire place is yours • 14 m² size • Kitchen
Best Price Match Harmony Medical Suites ChinaTown Best Price Match
8.3 (58 Reviews) Apartment
Apartments • Private parking • Pet friendly
Best Price Match Boston Monadnock Properties Best Price Match
8.6 (315 Reviews) Homestay
Free WiFi • Non-smoking rooms • Family rooms
Boston Dorchester • In Dewey Square · 4.0km to center
Best Price Match Villa Places to Stay in Dewey Square
Over 1+ Villa Places to Stay in or Near Dewey Square
Waterfront Escape - Close to Airport & Downtown Best Price Match
9.7 (3 Reviews) Villa
The entire place is yours • 242 m² size • Free on-site parking
Boston East Boston • In Dewey Square · 4.7km to center
Best Price Match Hotels in Dewey Square
Over 150+ Hotels in or Near Dewey Square
Seaport Hotel® Boston Best Price Match
9.1 (2786 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Boston South Boston • In Dewey Square · 1.3km to center
Best Price Match Club Quarters Hotel Faneuil Hall, Boston Best Price Match
8.4 (4031 Reviews) Hotel
Breakfast • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 405m to center
Best Price Match The Newbury Boston Best Price Match
9.0 (553 Reviews) Hotel
Breakfast • 2 restaurants • Pet friendly
Best Price Match The Verb Hotel Best Price Match
9.3 (2738 Reviews) Hotel
Breakfast • Private parking • Outdoor swimming pool
Best Price Match The Dagny Boston Best Price Match
9.0 (2262 Reviews) Hotel
2 restaurants • Pet friendly • Free WiFi
Boston Downtown Boston • In Dewey Square · 502m to center
Best Price Match The Whitney Hotel Boston Best Price Match
9.1 (1062 Reviews) Hotel
Private parking • Restaurant • Pet friendly
Boston Beacon Hill • In Dewey Square · 1.6km to center
Best Price Match The Godfrey Hotel Boston Best Price Match
9.0 (3506 Reviews) Hotel
Private parking • 2 restaurants • Pet friendly
Boston Downtown Boston • In Dewey Square · 526m to center
Best Price Match Cheap Places to Stay in Dewey Square
Over 150+ Cheap Places to Stay in or Near Dewey Square
HomeStay in Harvest Street Best Price Match
9.7 (28 Reviews) Bed_and_breakfast
Free on-site parking • Free WiFi • Non-smoking rooms
Boston Dorchester • In Dewey Square · 3.3km to center
Best Price Match 
Boston Homestel Best Price Match
8.0 (497 Reviews) Hostel
Private parking • Free WiFi • Shower
Boston Dorchester • In Dewey Square · 3.6km to center
Best Price Match 
Homestay in Boston Pearl Street Best Price Match
9.6 (17 Reviews) Bed_and_breakfast
Free on-site parking • Hot tub • Free WiFi
Boston Dorchester • In Dewey Square · 4.3km to center
Best Price Match 
HI Boston Hostel Best Price Match
8.6 (6790 Reviews) Hostel
Free WiFi • Private bathroom • Non-smoking rooms
Boston Boston Common • In Dewey Square · 686m to center
Best Price Match 
Hotel Ivy Boston Common Best Price Match
7.9 (3357 Reviews) Hotel
Free WiFi • Private bathroom • Non-smoking rooms
Boston Boston Common • In Dewey Square · 966m to center
Best Price Match 
citizenM Boston North Station Best Price Match
8.8 (4356 Reviews) Hotel
Breakfast • Restaurant • Free WiFi
Best Price Match 
DoubleTree by Hilton Hotel Boston Bayside Best Price Match
7.9 (1474 Reviews) Hotel
Breakfast • On-site parking • Restaurant
Boston Dorchester • In Dewey Square · 3.7km to center
Best Price Match 
Hampton Inn & Suites Boston Crosstown Center Best Price Match
7.6 (1112 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match About Dewey Square Vacation Rentals
Looking for places to stay in Dewey Square? Compare top options in Boston.
With more than 428 Dewey Square vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Dewey Square.
Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Dewey Square. Prices average US $313 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Dewey Square, with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Stay Categories in Dewey Square
Use These Quick Filters to Find a Vacation Rental in Dewey Square
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Dewey Square.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Dewey Square. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.
Weather in Dewey Square
Average temperatures and rainfall by month range to help plan your stay in Dewey Square.
Mar - May
Avg High14°C / 57°F
Avg Low4°C / 39°F
Rainfall102 mm / 4 in
Jun - Aug
Avg High27°C / 81°F
Avg Low17°C / 63°F
Rainfall98 mm / 3.9 in
Sep - Nov
Avg High17°C / 63°F
Avg Low8°C / 47°F
Rainfall102 mm / 4 in
Dec - Feb
Avg High4°C / 40°F
Avg Low-4°C / 24°F
Rainfall100 mm / 3.9 in