Villa Bay - Vacation Rentals in Dudley Square

Harmony Medical Suites on Canal From US $210
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Homestay In Fields Corner Area Boston From US $79
         

10.0 (2 Reviews)
Bed & Breakfast
  • Security/Safety
  • Restaurant
  • Guest Services
Great South End/Back Bay location, 1 bed condo near T station From US $414
         

10.0 (97 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Chic South End Studio With Patio From US $208
         

10.0 (103 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern townhome,Boston vacation,2 bath,pkg,deck From US $367
         

9.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated pet friendly apt by parks and train! From US $180
         

8.0 (35 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Dudley Square

Over 3108+ Luxury Places to Stay in or Near Dudley Square

Top-Rated Vacation Rentals with a Pool in Dudley Square

Over 352+ Top-Rated Vacation Rentals with a Pool in or Near Dudley Square
South End Club Suites by Orchard From US $344
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxurious 3-bedroom apartment in vibrant Boston
New
From US $420
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatus Luxury Residences Boston South Bay Designer Collection From US $361
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Dudley Square

Over 1551+ Pet-Friendly Vacation Rentals in or Near Dudley Square
Boston vacation,Longwood Medical,mins to MBTA,pkg From US $144
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluebird Suites near MIT From US $143
         

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8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston Harbor Hotel From US $568
         

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9.8 (1006 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Furnished Delx Studio w/Full Kitchen & Fast WiFi | Boston From US $153
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Excellent 2 bedroom condo in South Boston From US $349
         

Right Near Convention Center and Train Station From US $451
         

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10.0 (28 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
14a-Cozy and well decorated apartment in awesome Boston From US $498
         

10.0 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Heart of Southie - Hot Tub + Walk to Top Bars From US $809
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Dudley Square

Over 278+ Large Vacation Homes & Villas in or Near Dudley Square
The Upton From US $129
         

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6.5 (13 Reviews)
Apartment
  • Air Conditioner
  • Breakfast
  • Internet
15 minutes to Historic Sights and World Cup Transport. From US $850
         

Spacious, New Renovation | Near T From US $800
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
558/2 - 3BR Boston - Modern Nest near Franklin Park From US $414
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Mid-Century Glam Retreat, Near T From US $356
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Dudley Square

Over 1408+ Wheelchair Accessible Vacation Homes in or Near Dudley Square
Sunlit Spacious 3BR in Heart of Downtown Boston! Guest Favorite! From US $548
         

10.0 (57 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Bluebird Suites in Kendall Square From US $169
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The College Club of Boston From US $229
         

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9.4 (1011 Reviews)
Bed & Breakfast
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
Bright & Spacious Loft Steps to the Freedom Trail From US $363
         

10.0 (52 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
King Bed Loft in the Heart of Downtown Boston From US $334
         

10.0 (37 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Back-Bay Upscale Central Condo Bos Common Downtown From US $463
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Back-Bay Lux Central 2BR Condo with Rooftop and Parking From US $420
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Charming Spacious 3BR+2BA ◆ Downtown Boston ◆ Family Favorite From US $678
         

Dudley Square Varoom and Airbnb Places to Stay Under $200

Over 847+ Dudley Square Varoom and Airbnb Places to Stay Under $200
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Chic Modern 2 bed Apartment with Exposed Brick From US $160
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Homestay In Boston - From US $72
         

10.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Bedding/Linens
  • Fireplace/Heating
Charming room in a 2-bedroom townhome with AC, WiFi in fantastic central Boston From US $177
         

I New apartment with Luxury amenities in Boston. From US $188
         

10.0 (2 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • Bedding/Linens
Sunny,spacious, sleeps 4, steps to MBTA,Hospitals. From US $160
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The Arcadian powered by Sonder | Double Bunk Room w/Corridor View From US $196
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $177
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Dudley Square

Over 1866+ Instantly Bookable Vacation Homes in or Near Dudley Square
Entire Apt Downton Seaport (BEN-2010) From US $496
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Stunning South End/Back Bay Penthouse! From US $542
         

10.0 (96 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beautiful Boston Brownstone! From US $533
         

10.0 (83 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
UltraLuxe Apt in Boston Brownstone in Prime Area From US $550
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
🎖The Ashmont Suite - Close to Subway + Downtown🎖 From US $264
         

Hidden Gem 2 BR/1BA near Zoo 3 mil downtown Fenway From US $334
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

About Dudley Square Vacation Rentals

With more than 3117 Dudley Square vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villa Bay and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Dudley Square.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villa Bay Dudley Square, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Dudley Square. Places to stay near Dudley Square are 556.74 ft² on average, with prices averaging $405 a night.

Villa Bay makes it easy and safe to find and compare vacation rentals in Dudley 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 Rental Accommodation Types in Dudley Square

Type Count
Holiday Apartments 2163
Vacation Homes 416
Hotels with Suites 374
B&B 12
Hostels 3
Others 1
Resorts 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Dudley Square

Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Dudley Square.

Weather in Dudley Square

View the weather forecast for Dudley Square before booking your Dudley Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F