Dudley Square Holiday Rentals

Compare Villas, Resorts, & Rentals in Dudley Square, Boston, Massachusetts, USA

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10.0 (5 Reviews)
10 Bedrooms 24 Guests
From CA $211 per night
9.6 (1224 Reviews)
1 Bedroom 2 Guests
New 5BR3B Lux Home Walk to Subway Near Downtown
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10.0 (3 Reviews)
4 Bedrooms 13 Guests
From CA $521 per night
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9.4 (1004 Reviews)
1 Bedroom 2 Guests
New Elegant 3BR 2BA Condo Seaport Boston.
From CA $1,333 per night
New
3 Bedrooms 6 Guests
From CA $2,294 per night
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
From CA $792 per night
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9.2 (242 Reviews)
1 Bedroom 2 Guests
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10.0 (2 Reviews)
1 Bedroom 4 Guests
New Stylish South End Penthouse Stunning City Views
New
2 Bedrooms 2 Guests
From CA $474 per night
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10.0 (2 Reviews)
3 Bedrooms 10 Guests
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
New Raffles Pied-A-Tier Studio
From CA $369 per night
New
1 Bedroom 2 Guests
From CA $1,413 per night
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10.0 (1 Review)
2 Bedrooms 4 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
From CA $595 per night
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10.0 (1 Review)
4 Bedrooms 8 Guests
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10.0 (1 Review)
3 Bedrooms 13 Guests
From CA $475 per night
10.0 (99 Reviews)
1 Bedroom 2 Guests
From CA $289 per night
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10.0 (1 Review)
4 Bedrooms 11 Guests
10.0 (95 Reviews)
1 Bedroom 2 Guests
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10.0 (1 Review)
5 Bedrooms 13 Guests
10.0 (90 Reviews)
2 Bedrooms 4 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
From CA $755 per night
10.0 (78 Reviews)
2 Bedrooms 4 Guests
From CA $681 per night
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10.0 (1 Review)
1 Bedroom 2 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
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10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (48 Reviews)
1 Bedroom 4 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (35 Reviews)
1 Bedroom 4 Guests
10.0 (1 Review)
1 Bedroom 6 Guests
10.0 (32 Reviews)
2 Bedrooms 9 Guests
10.0 (25 Reviews)
1 Bedroom 3 Guests
10.0 (22 Reviews)
1 Bedroom 2 Guests
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10.0 (21 Reviews)
2 Bedrooms 7 Guests
10.0 (17 Reviews)
2 Bedrooms 4 Guests
From CA $298 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
From CA $317 per night
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9.0 (1828 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
From CA $1,440 per night
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9.9 (8 Reviews)
5 Bedrooms 16 Guests
From CA $315 per night
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8.8 (270 Reviews)
1 Bedroom 2 Guests
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9.8 (16 Reviews)
4 Bedrooms 10 Guests
From CA $220 per night
8.6 (88 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
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9.7 (4 Reviews)
3 Bedrooms 13 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
From CA $1,103 per night
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9.7 (4 Reviews)
3 Bedrooms 6 Guests
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9.6 (10 Reviews)
8 Bedrooms 4 Guests
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9.6 (9 Reviews)
2 Bedrooms 6 Guests
From CA $829 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
From CA $638 per night
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9.6 (8 Reviews)
3 Bedrooms 6 Guests
10.0 (1 Review)
2 Bedrooms 3 Guests
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9.6 (7 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
From CA $335 per night
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9.5 (14 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
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9.5 (2 Reviews)
2 Bedrooms 4 Guests
From CA $1,185 per night
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9.5 (2 Reviews)
2 Bedrooms 8 Guests

About Casai's Private Villas and Holiday Rentals in Dudley Square

Discover more than 2962 vacation rentals available in Dudley Square. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Dudley Square.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Dudley Square, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Dudley Square. On average, places to stay near Dudley Square offer 583.81 ft², with nightly prices averaging CA $602.

With Casai, finding and comparing holiday rentals in Dudley Square is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Dudley Square?

What are the top holiday rentals in Dudley Square?

How many Casai.ca holiday rentals are available in Dudley Square?

As of 2025, Casai boasts over 2962 properties listed in the Dudley Square area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Dudley Square.

Nearby Neighborhood (3)

Neighborhood Property Count
Roxbury Vacation Rentals in Boston, Massachusetts 80
Washington Park Vacation Rentals in Boston, Massachusetts 28
Dudley - Brunswick King Vacation Rentals in Boston, Massachusetts 2634