Dudley Square pickleball Stays, Resort Rentals, & Homes
Apartment
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
750 ft²
Parking
Kitchen
Air Conditioner
Internet
US $434/Night
7 Nights - US $3,039
House
- Boston
- ·
- Telegraph Hill
- 0.25 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
13 Guests
1797.57 ft²
- Parking
Spa
View- Air Conditioner
US $1,586/Night
7 Nights - US $11,102
House
- Boston
- ·
- Fenway–Kenmore
- 0.55 mi to center
9.4Exceptional
(1471 Reviews)
1 Bedroom
1 Bath
- Parking
Balcony/Terrace- Air Conditioner
- Internet
US $230/Night
7 Nights - US $1,609
Apartment
- Boston
- ·
- Aspinwall Hill
- 0.16 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $136/Night
7 Nights - US $951
Apartment
- Boston
- ·
- Downtown Boston
- 0.29 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
5963.21 ft²
- Air Conditioner
- Internet
Pet Friendly
Child Friendly
US $2,029/Night
7 Nights - US $14,205
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $545/Night
7 Nights - US $3,816
Apartment
- Boston
- ·
- Emerson Gardens
- 0.16 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $132/Night
7 Nights - US $922
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $568/Night
7 Nights - US $3,973
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $430/Night
7 Nights - US $3,010
Luxury Places to Stay in Dudley Square
Over 3633+ Luxury Places to Stay in or Near Dudley Square
Unlock the Best Price
Unlock the Best Price
US $9,322/Night
7 Nights - US $65,257
US $9,322/Night
7 Nights - US $65,257
House
4 Bedrooms
4 Baths
8 Guests
Security/Safety
US $6,010/Night
7 Nights - US $42,071
US $4,063/Night
7 Nights - US $28,441
US $4,063/Night
7 Nights - US $28,441
House
- Boston
- ·
- Back Bay West
- 0.12 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
11 Guests
3869 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,755/Night
7 Nights - US $26,282
US $3,273/Night
7 Nights - US $22,911
Top-Rated Villas with a Pool in Dudley Square
Over 440+ Top-Rated Private Villas with a Pool in or Near Dudley Square
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(3 Reviews)
4 Baths
Breakfast- Parking
Pool- Kitchen
US $900/Night
7 Nights - US $6,300
Hotel
10.0Exceptional
(2 Reviews)
2 Baths
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $482/Night
7 Nights - US $3,371
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
10 Guests
904.17 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $344/Night
7 Nights - US $2,408
Hotel
10.0Exceptional
(2 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $243/Night
7 Nights - US $1,702
Apartment
- Boston
- ·
- Seaport District
- 0.17 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
5 Guests
1205.56 ft²
Oceanfront- Parking
- Pool
Ocean View
US $808/Night
7 Nights - US $5,657
Hotel
10.0Exceptional
(1 Review)
4 Baths
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $737/Night
7 Nights - US $5,162
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(1 Review)
3 Baths
- Breakfast
- Parking
- Pool
- Kitchen
US $697/Night
7 Nights - US $4,882
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(1 Review)
3 Baths
- Breakfast
- Parking
- Pool
- Kitchen
US $689/Night
7 Nights - US $4,826
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(1 Review)
3 Baths
- Breakfast
- Parking
- Pool
- Kitchen
US $689/Night
7 Nights - US $4,826
Pet-Friendly Villas in Dudley Square
Over 1903+ Pet-Friendly Private Villas in or Near Dudley Square
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $225/Night
7 Nights - US $1,578
Apartment
- Boston
- ·
- Codman Square
- 0.26 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
1 Bath
11 Guests
1399.31 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $549/Night
7 Nights - US $3,841
Hotel
- Boston
- ·
- Waterfront
- 0.18 mi to center
9.8Exceptional
(1013 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $809/Night
7 Nights - US $5,666
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $221/Night
7 Nights - US $1,547
Apartment
- Boston
- ·
- Harrison Lenox
- 0.50 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $360/Night
7 Nights - US $2,520
Apartment
9.6Exceptional
(55 Reviews)
2 Bedrooms
1 Bath
6 Guests
637 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $450/Night
7 Nights - US $3,149
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $375/Night
7 Nights - US $2,627
Apartment
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $194/Night
7 Nights - US $1,358
Apartment
9.4Exceptional
(48 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $180/Night
7 Nights - US $1,260
Large Private Villas in Dudley Square
Over 322+ Large Villas in or Near Dudley Square for Groups and Families
House
- Boston
- ·
- Upham's Corner
- 0.29 mi to center
6.8Good
(3 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $555/Night
7 Nights - US $3,886
House
- Boston
- ·
- Egleston Square
- 0.36 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
2 Baths
9 Guests
2002.09 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $801/Night
7 Nights - US $5,604
Apartment
- Boston
- ·
- D Street - West Broadway
- 0.63 mi to center
2 Bedrooms
2 Baths
90 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $715/Night
7 Nights - US $5,007
Apartment
- Boston
- ·
- Dorchester
- 0.40 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
15 Guests
1302.43 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $593/Night
7 Nights - US $4,152
Condo
- Boston
- ·
- Griggs Park
- 0.02 mi to center
10.0Exceptional
(6 Reviews)
4 Bedrooms
4 Baths
10 Guests
1001 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $2,715/Night
7 Nights - US $19,008
Apartment
- Boston
- ·
- Griggs Park
- 0.03 mi to center
9.6Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,501/Night
7 Nights - US $10,507
Apartment
- Boston
- ·
- High Street Hill
- 0.18 mi to center
9.4Exceptional
(46 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $543/Night
7 Nights - US $3,802
New
Apartment
- Boston
- ·
- Griggs Park
- 0.15 mi to center
8.0Excellent
(1 Review)
4 Bedrooms
4 Baths
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,230/Night
7 Nights - US $8,609
House
- Boston
- ·
- High Street Hill
- 0.14 mi to center
6 Bedrooms
2 Baths
14 Guests
- Parking
- Kitchen
- Internet
- Pet Friendly
US $1,215/Night
7 Nights - US $8,507
Wheelchair Accessible Holiday Homes in Dudley Square
Over 1554+ Wheelchair Accessible Villas and Holiday Homes in or Near Dudley Square
Condo
9.4Exceptional
(24 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $412/Night
7 Nights - US $2,887
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
11 Guests
631.48 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $210/Night
7 Nights - US $1,470
Bed & Breakfast
- Boston
- ·
- Back Bay East
- 0.19 mi to center
9.4Exceptional
(1004 Reviews)
1 Bedroom
1 Bath
- Air Conditioner
- Internet
- Child Friendly
Wheelchair Accessible
US $309/Night
7 Nights - US $2,164
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $247/Night
7 Nights - US $1,726
Apartment
- Boston
- ·
- Harrison Lenox
- 0.50 mi to center
9.5Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1001.04 ft²
- Parking
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
US $399/Night
7 Nights - US $2,793
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
8.6Fabulous
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $224/Night
7 Nights - US $1,567
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
7.4Very Good
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $224/Night
7 Nights - US $1,567
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
7.0Very Good
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $258/Night
7 Nights - US $1,806
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
5.0Average
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $231/Night
7 Nights - US $1,617
Dudley Square Villas, Airbnb and Holiday Homes Under $200
Over 847+ Dudley Square Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- Boston
- ·
- Coolidge Corner South Side
- 0.25 mi to center
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
450 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $139/Night
7 Nights - US $970
Apartment
- Boston
- ·
- East Cambridge
- 0.40 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
13 Guests
9752.1 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $124/Night
7 Nights - US $868
Bed & Breakfast
- Boston
- ·
- Dorchester
- 1.66 mi to center
8.4Excellent
(50 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Kitchen
- Internet
- Child Friendly
US $120/Night
7 Nights - US $837
Apartment
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $154/Night
7 Nights - US $1,077
Apartment
- Boston
- ·
- Downtown Boston
- 0.29 mi to center
9.2Exceptional
(42 Reviews)
2 Bedrooms
1 Bath
4 Guests
1076.39 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $160/Night
7 Nights - US $1,118
Apartment
8.8Fabulous
(13 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $180/Night
7 Nights - US $1,260
Apartment
7.8Very Good
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $139/Night
7 Nights - US $973
Apartment
- Boston
- ·
- North Brookline
- 0.35 mi to center
2 Bedrooms
1 Bath
4 Guests
1066 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $199/Night
7 Nights - US $1,396
Apartment
- Boston
- ·
- North Brookline
- 0.35 mi to center
2 Bedrooms
1 Bath
4 Guests
1060 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $190/Night
7 Nights - US $1,332
Instantly Bookable Villa Rentals in Dudley Square
Over 2212+ Instantly Bookable Private Villas in or Near Dudley Square
Apartment
- Boston
- ·
- Aspinwall Hill
- 0.12 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Internet
- Pet Friendly
US $481/Night
7 Nights - US $3,366
Apartment
- Massachusetts
- ·
- Boston
- 0.83 mi to center
1 Bedroom
1 Bath
- Pool
- Kitchen
- Air Conditioner
- Internet
US $496/Night
7 Nights - US $3,475
Apartment
- Boston
- ·
- North Brookline
- 0.36 mi to center
5.0Average
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
904 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $221/Night
7 Nights - US $1,547
Apartment
- Boston
- ·
- Coolidge Corner South Side
- 0.13 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $730/Night
7 Nights - US $5,111
Apartment
- Boston
- ·
- North Brookline
- 0.60 mi to center
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $469/Night
7 Nights - US $3,286
Apartment
- Boston
- ·
- North Brookline
- 0.22 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $431/Night
7 Nights - US $3,018
New
House
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $430/Night
7 Nights - US $3,009
Apartment
- Boston
- ·
- North Brookline
- 0.24 mi to center
1 Bedroom
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $427/Night
7 Nights - US $2,987
Apartment
- Boston
- ·
- Coolidge Corner South Side
- 0.24 mi to center
1 Bedroom
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $418/Night
7 Nights - US $2,924
Book a Last Minute Place to Stay in Dudley Square
About Dudley Square Vacation Rentals
Discover over 3642 amazing vacation rental options in Dudley Square with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Dudley Square.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 567.62 ft², with prices averaging US $429 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Dudley Square.
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Top Pickleball-Ready Accommodation Types in Dudley Square
| Type | Count |
|---|---|
| Holiday Apartments | 2631 |
| Vacation Homes | 450 |
Use these Quick Filters to Find a Vacation Rental in Dudley Square
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Dudley Square with PickleTrip™.
Weather in Dudley Square, MA
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
Frequently Asked Questions About Dudley Square?
What are the top vacation rentals, resorts, and hotels in Dudley Square with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Dudley Square. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Dudley Square!
- Historic Townhouse Condo in the center of Boston, across from the Public Garden
- Airy new apt for 2-6. Off-street parking. Walk to shops/restaurants/subway/bus
- Stunning South End/Back Bay Penthouse!
- Great South End/Back Bay location, 1 bed condo near T station
- Chic South End Studio With Patio
- Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
- Beautiful Boston Brownstone!
- The Heart of Southie (Garage + Roof Deck)
- Spacious Sunlit 3BR Center of Downtown Boston Family Favorite
- 🎖The Ashmont Suite - Close to Subway + Downtown🎖
How many pickleball-ready properties have private pools in Dudley Square?
Discover 40 accommodations with private or nearby pickleball courts in Dudley Square. Some of the best destinations to stay and play pickleball are:
- Large 2 Bed/2Bath By MGH, Washer/Dryer in Suite
- Blueground South End gym nr groceries shops BOS-1021
- Stunning Rooftop Apartment & Garden Deck
- Vibrant Two Bed steps from Charles River
Which vacation rentals, resorts, or hotels in Dudley Square is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Dudley Square? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
How many PickleTrip vacation rentals or resorts are available in Dudley Square?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 3642 properties listed in Dudley Square in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Roxbury Vacation Rentals in Boston, Massachusetts | 113 |
| Washington Park Vacation Rentals in Boston, Massachusetts | 34 |
| Dudley - Brunswick King Vacation Rentals in Boston, Massachusetts | 3302 |
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