Vacation Rentals in Dudley Square, MA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Boston
  6.  Dudley Square

Refine your search

Price per night

Amenity Filter

Rating

2290 Best Vacation Rentals in Dudley Square (Starting from $120)

Perrin Place Unit 1
Perrin Place Unit 1
Apartment
Boston, MA, USA
0.2k from Dudley Square center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

5 Bedrooms12 Guests
8.7

Fabulous

32 reviews

$344
Average price / night
Check Availability
3BD/Free Parking/Stocked Kitchen/10 min -> Boston
3BD/Free Parking/Stocked Kitchen/10 min -> Boston
Apartment
Boston, MA, 02119, United States
0.2k from Dudley Square center

AC, Dryer, Heater, Internet, Laundry, No Smoking

3 Bedrooms6 Guests
6.8

Good

3 reviews

$348
Average price / night
Check Availability
Perrin Place Unit 3
Perrin Place Unit 3
Apartment
Boston, MA, USA
0.2k from Dudley Square center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Self-catering

3 Bedrooms6 Guests
8.6

Fabulous

26 reviews

$430
Average price / night
Check Availability
Sunny Artist Loft
Sunny Artist Loft
Apartment
Boston, MA, 02119, United States
0.2k from Dudley Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom30 Guests
New to Booking
$120
Average price / night
Check Availability
Boston Luxury 3 bedroom Private Condo
Boston Luxury 3 bedroom Private Condo
Apartment
Boston, MA, USA
0.4k from Dudley Square center

Apartments, Luxury, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms6 Guests
9.1

Superb

12 reviews

$230
Average price / night
Check Availability
Upscale Unit 1 at Perrin Place
Upscale Unit 1 at Perrin Place
Apartment
Boston, MA, 02119, United States
0.2k from Dudley Square center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
9.2

Superb

47 reviews

$343
Average price / night
Check Availability
Brand New Luxury Rooms near downtown Boston
Brand New Luxury Rooms near downtown Boston
House
Boston, MA, USA
0.4k from Dudley Square center

B&bs, Luxury, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals

10 Bedrooms4 Guests
8.9

Fabulous

161 reviews

$139
Average price / night
Check Availability
Boston Modern Escape I Minutes to Downtown & South End
Boston Modern Escape I Minutes to Downtown & South End
Apartment
Boston, MA, 02119, United States
0.3k from Dudley Square center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$321
Average price / night
Check Availability
NEW! Boston Entire House Near MBTA, 3 Mi to Fenway!
NEW! Boston Entire House Near MBTA, 3 Mi to Fenway!
Apartment
Boston, MA, USA
0.5k from Dudley Square center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

8 Bedrooms16 Guests
8.8

Fabulous

4 reviews

$540
Average price / night
Check Availability
NEW! Spacious Modern 3BR - FREE Parking - Heart of Boston
NEW! Spacious Modern 3BR - FREE Parking - Heart of Boston
Apartment
Boston, MA, 02121, United States
0.3k from Dudley Square center

3 Bedrooms9 Guests
New to Booking
$1245
Average price / night
Check Availability
NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)
NEW! Boston Condo Near MBTA, 3Mi to Fenway ! (U3)
Apartment
Boston, MA, USA
0.5k from Dudley Square center

Entertainment, Sports/Activities, Parking, Air Conditioner, Security/Safety, Fireplace/Heating, Internet

3 Bedrooms6 Guests
6.8

Good

23 reviews

$257
Average price / night
Check Availability
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Apartment
Boston, MA, 02119, United States
0.3k from Dudley Square center

AC, Crib, Free Parking, Heater, Internet, Kitchen, No Smoking, Outdoor Space, Toys

1 Bedroom4 Guests
9.8

Exceptional

46 reviews

$231
Average price / night
Check Availability
NEW! Boston Condo Near MBTA, 3 Mi to Fenway! (U2)
NEW! Boston Condo Near MBTA, 3 Mi to Fenway! (U2)
Apartment
Boston, MA, USA
0.5k from Dudley Square center

Internet, Air Conditioner, Guest Services, Security/Safety, Parking, Child Friendly

3 Bedrooms6 Guests
7.8

Good

14 reviews

$309
Average price / night
Check Availability
Upscale Unit 3 at Perrin Place
Upscale Unit 3 at Perrin Place
Apartment
Boston, MA, 02119, United States
0.4k from Dudley Square center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

48 reviews

$432
Average price / night
Check Availability
NEW! Boston Condo Near MBTA, 3Mi to Fenway! (U1)
NEW! Boston Condo Near MBTA, 3Mi to Fenway! (U1)
Apartment
Boston, MA, USA
0.5k from Dudley Square center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Self-catering, Condos

2 Bedrooms4 Guests
7.3

Good

4 reviews

$195
Average price / night
Check Availability
In-Unit Laundry Your Family and Friends Space
In-Unit Laundry Your Family and Friends Space
Apartment
Boston, MA, USA
0.9k from Dudley Square center

Apartments, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom13 Guests
4.5

Review score

2 reviews

$315
Average price / night
Check Availability
Esjacpe Guest House 3
Esjacpe Guest House 3
House
Boston, MA, USA
0.9k from Dudley Square center

B&bs, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$141
Average price / night
Check Availability
NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
House
Boston, MA, 02125, United States
0.5k from Dudley Square center

AC, Free Parking, Heater, Internet, Microwave, No Smoking, Outdoor Space, Patio, Toys

8 Bedrooms16 Guests
10.0

Exceptional

5 reviews

$900
Average price / night
Check Availability
Spectacular Boston City View
Spectacular Boston City View
Apartment
MA, USA
1.0k from Dudley Square center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family, Self-catering

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$463
Average price / night
Check Availability
Extremely clean and Affordable.
Extremely clean and Affordable.
Apartment
Boston, MA, 02119, United States
0.6k from Dudley Square center

AC, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Toys

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$241
Average price / night
Check Availability
Great 1-bedroom apartment in superb Boston with fitness room, WiFi
Great 1-bedroom apartment in superb Boston with fitness room, WiFi
Apartment
Boston, MA, 02119, United States
0.6k from Dudley Square center

Dryer, Fitness Equipment, Internet, Laundry, Living Area, No Smoking, Washer

1 Bedroom4 Guests
7.0

Good

4 reviews

$183
Average price / night
Check Availability
Furnished 3- Bedrooms near Hospitals & Universities in vibrant Boston w/ Wifi.
Furnished 3- Bedrooms near Hospitals & Universities in vibrant Boston w/ Wifi.
House
Boston, MA, 02119, United States
0.6k from Dudley Square center

AC, Heater, Internet, Laundry, No Smoking

3 Bedrooms4 Guests
New to Booking
$287
Average price / night
Check Availability
Beautiful, Budget-Friendly Apt. l Steps to Free Buses and Minutes to Downtown
Beautiful, Budget-Friendly Apt. l Steps to Free Buses and Minutes to Downtown
Apartment
Boston, MA, 02119, United States
0.6k from Dudley Square center

Heater, No Smoking

3 Bedrooms6 Guests
New to Booking
$355
Average price / night
Check Availability
Nightingale In Boston
Nightingale In Boston
Apartment
Boston, MA, 02119, United States
0.6k from Dudley Square center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

New to Booking
$345
Average price / night
Check Availability
Historic Brownstone Elegance: Blue Colonial Suite
Historic Brownstone Elegance: Blue Colonial Suite
Apartment
Boston, MA, 02119, United States
0.6k from Dudley Square center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$512
Average price / night
Check Availability
Spacious 3BR Apartment for 8 | Heart of Boston
Spacious 3BR Apartment for 8 | Heart of Boston
Apartment
Boston, MA, 02119, United States
0.7k from Dudley Square center

AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave

3 Bedrooms8 Guests
New to Booking
$1422
Average price / night
Check Availability
Historic 2 floor Apt in Boston w/ outdoor deck!
Historic 2 floor Apt in Boston w/ outdoor deck!
Apartment
Boston, MA, 02119, United States
0.8k from Dudley Square center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms8 Guests
New to Booking
$918
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Dudley Square.

Stay Near Dudley Square's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Dudley Square Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2290 verified vacation rentals in Dudley Square. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Dudley Square vary depending on the season, property size, and location. Rates typically start from around $120 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Dudley Square include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Dudley Square welcome pets. Currently, 18 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Dudley Square often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.