Cruise And Resorts - Vacation Rentals in Dudley Square

Capricornus: Oceanside Vacation From US $627
         

9.2 (41 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • TV
Joy Ride: A Waterfront Getaway From US $292
         

9.4 (6 Reviews)
Boat Rental
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Dudley Square

Over 3381+ Luxury Places to Stay in or Near Dudley Square

Top-Rated Vacation Rentals with a Pool in Dudley Square

Over 361+ Top-Rated Vacation Rentals with a Pool in or Near Dudley Square
Hyatus Luxury Residences Boston South Bay Designer Collection From US $361
         

|
10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
A short drive from Old State House! Balcony! Parking! From US $394
         

South End Club Suites by Orchard From US $344
         

|
10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston pad: 2BR suite with pool and gym From US $1,087
         

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

Pet-Friendly Vacation Rentals in Dudley Square

Over 1729+ Pet-Friendly Vacation Rentals in or Near Dudley Square
Modern Townhome - Boston Vacation with 2 Bath, Parking and a Deck From US $428
         

Harmony Medical Suites on Canal From US $210
         

|
10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston Harbor Hotel From US $537
         

|
9.8 (1008 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated pet friendly apt by parks and train! From US $251
         

8.0 (36 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 Bedroom unit with central air in Brookline Village - Near Longwood From US $398
         

Boston vacation,Longwood Medical,mins to MBTA,pkg From US $182
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Excellent 2 bedroom condo in South Boston From US $376
         

Right Near Convention Center and Train Station From US $529
         

10.0 (29 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Dudley Square

Over 285+ Large Vacation Homes & Villas in or Near Dudley Square
The Upton From US $129
         

|
6.5 (13 Reviews)
Apartment
  • Air Conditioner
  • Breakfast
  • Internet
City's Hippest Neighborhood. n From US $886
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Heart of Southie - Hot Tub + Walk to Top Bars From US $1,093
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious, New Renovation | Near T From US $684
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Mid-Century Glam Retreat, Near T From US $625
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Dudley Square

Over 1500+ Wheelchair Accessible Vacation Homes in or Near Dudley Square
Furnished Delx Studio w/Full Kitchen & Fast WiFi | Boston From US $147
         

Bluebird Suites near MIT From US $143
         

|
8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The College Club of Boston From US $194
         

|
9.4 (1004 Reviews)
Bed & Breakfast
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
Spacious 3BR in Heart of Downtown Boston! Walk-Everywhere! From US $616
         

10.0 (58 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Bright & Spacious Loft Steps to the Freedom Trail From US $337
         

10.0 (52 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
King Bed Loft in the Heart of Downtown Boston From US $1,295
         

10.0 (38 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Back-Bay Upscale Central Condo Bos Common Downtown From US $511
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Back-Bay Lux Central 2BR Condo with Rooftop and Parking From US $982
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Dudley Square Varoom and Airbnb Places to Stay Under $200

Over 805+ 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 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluebird Suites in Kendall Square From US $169
         

|
New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Oasis Guest House From US $130
         

9.4 (1409 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Boston Harbor 1 BR | Desk+Wi-Fi | Kitchen From US $194
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 1BR | Full Kitchen | Work Desk & WiFi | by GLS From US $189
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely & Cozy Boston 2BR in FIDI | Downtown From US $175
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Convenient Beacon Hill 1BR near Mass Gen Hospital From US $173
         

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

Instantly Bookable Vacation Homes in Dudley Square

Over 2083+ 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
Great South End/Back Bay location, 1 bed condo near T station From US $467
         

10.0 (97 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Chic South End Studio With Patio From US $391
         

10.0 (103 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Stunning South End/Back Bay Penthouse! From US $559
         

10.0 (100 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beautiful Boston Brownstone! From US $534
         

10.0 (85 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
🎖The Ashmont Suite - Close to Subway + Downtown🎖 From US $524
         

About Dudley Square Vacation Rentals

With more than 3 Dudley Square vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts 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 Cruiseandresorts 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 with prices averaging $382 a night.

Cruiseandresorts 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

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

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts 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