3525+ Perfect Pickle Stays with Nearby Pickleball Facilities |
Dudley Square pickleball Stays, Resort Rentals, & Homes
Apartment
- Boston
- ·
- Jamaica Plain
- 0.43 mi to center
9.6Exceptional
(148 Reviews)
2 Bedrooms
1 Bath
5 Guests
800 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $254/Night
7 Nights - US $1,778
House
- Boston
- ·
- Telegraph Hill
- 0.25 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
13 Guests
1797.57 ft²
Spa- Fireplace/Heating
View
Pet Friendly
US $1,586/Night
7 Nights - US $11,102
House
- Boston
- ·
- Fenway–Kenmore
- 0.55 mi to center
9.4Exceptional
(1409 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Parking
Air Conditioner
US $130/Night
7 Nights - US $909
New
Apartment
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
US $2,102/Night
7 Nights - US $14,714
Apartment
- Boston
- ·
- Downtown Boston
- 0.29 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
4650.01 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $1,665/Night
7 Nights - US $11,653
New
Apartment
- Boston
- ·
- Dudley Square
- 0.42 mi to center
3 Bedrooms
2 Baths
8 Guests
2282 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,305/Night
7 Nights - US $9,135
Apartment
- Boston
- ·
- Highland Park
- 0.20 mi to center
3 Bedrooms
2 Baths
10 Guests
1399 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,206/Night
7 Nights - US $8,441
New
Apartment
- Boston
- ·
- Highland Park
- 0.20 mi to center
1 Bedroom
2 Baths
6 Guests
1593 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,134/Night
7 Nights - US $7,935
Apartment
- Boston
- ·
- Highland Park
- 0.20 mi to center
3 Bedrooms
2 Baths
10 Guests
1206 ft²
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $978/Night
7 Nights - US $6,845
Luxury Places to Stay in Dudley Square
Over 3516+ Luxury Places to Stay in or Near Dudley Square
Hotel
- Boston
- ·
- Back Bay East
- 0.28 mi to center
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
Unlock the Best Price
Hotel
- Boston
- ·
- Back Bay East
- 0.28 mi to center
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
Unlock the Best Price
US $9,423/Night
7 Nights - US $65,962
US $9,423/Night
7 Nights - US $65,962
House
4 Bedrooms
4 Baths
8 Guests
Security/Safety
US $5,633/Night
7 Nights - US $39,428
US $5,313/Night
7 Nights - US $37,188
Hotel
- Boston
- ·
- Back Bay East
- 0.28 mi to center
4 Baths
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $5,278/Night
7 Nights - US $36,943
House
- Boston
- ·
- Jones Hill
- 0.16 mi to center
9.2Exceptional
(7 Reviews)
12 Bedrooms
6 Baths
40 Guests
4657 ft²
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $4,068/Night
7 Nights - US $28,477
US $3,985/Night
7 Nights - US $27,894
Top-Rated Villas with a Pool in Dudley Square
Over 425+ Top-Rated Private Villas with a Pool in or Near Dudley Square
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(7 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $352/Night
7 Nights - US $2,462
Hotel
- Boston
- ·
- Bay Village
- 0.13 mi to center
10.0Exceptional
(2 Reviews)
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $1,317/Night
7 Nights - US $9,219
Hotel
10.0Exceptional
(2 Reviews)
2 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $870/Night
7 Nights - US $6,090
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1194.79 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
US $439/Night
7 Nights - US $3,072
Hotel
10.0Exceptional
(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $435/Night
7 Nights - US $3,048
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
10 Guests
904.17 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $344/Night
7 Nights - US $2,408
Hotel
10.0Exceptional
(1 Review)
4 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $1,786/Night
7 Nights - US $12,504
Apartment
- Boston
- ·
- Cambridgeport
- 0.12 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
12 Guests
1000 ft²
Hot Tub- Fireplace/Heating
- Pool
- Ocean View
US $1,576/Night
7 Nights - US $11,030
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
5 Guests
750 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $1,506/Night
7 Nights - US $10,540
Pet-Friendly Villas in Dudley Square
Over 1804+ Pet-Friendly Private Villas in or Near Dudley Square
Condo
- Boston
- ·
- D Street - West Broadway
- 0.70 mi to center
10.0Exceptional
(33 Reviews)
2 Bedrooms
1 Bath
7 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $536/Night
7 Nights - US $3,750
Apartment
- Boston
- ·
- Harrison Lenox
- 0.50 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1001.04 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $360/Night
7 Nights - US $2,520
Hotel
- Boston
- ·
- Waterfront
- 0.18 mi to center
9.8Exceptional
(1007 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $795/Night
7 Nights - US $5,563
Condo
- Boston
- ·
- South Boston
- 0.58 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $638/Night
7 Nights - US $4,469
Apartment
- Boston
- ·
- Downtown Boston
- 0.29 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1076.39 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,118
Apartment
- Boston
- ·
- Beacon Hill
- 0.24 mi to center
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
2 Guests
1050 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $333/Night
7 Nights - US $2,331
Apartment
- Boston
- ·
- Jamaica Plain
- 1.33 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $153/Night
7 Nights - US $1,072
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $379/Night
7 Nights - US $2,653
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
759 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $268/Night
7 Nights - US $1,875
Large Private Villas in Dudley Square
Over 314+ Large Villas in or Near Dudley Square for Groups and Families
Apartment
- Boston
- ·
- Cambridgeport
- 0.03 mi to center
2 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,516/Night
7 Nights - US $10,612
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
11 Guests
631.48 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $210/Night
7 Nights - US $1,470
Apartment
- Boston
- ·
- D Street - West Broadway
- 0.63 mi to center
2 Bedrooms
2 Baths
90 Guests
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $644/Night
7 Nights - US $4,505
Apartment
- Boston
- ·
- East Cambridge
- 0.40 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
13 Guests
9752.1 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $124/Night
7 Nights - US $868
Condo
- Boston
- ·
- Griggs Park
- 0.02 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
10 Guests
1001 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,559/Night
7 Nights - US $10,914
Apartment
- Boston
- ·
- Griggs Park
- 0.03 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $2,663/Night
7 Nights - US $18,641
Apartment
- Boston
- ·
- High Street Hill
- 0.18 mi to center
9.4Exceptional
(43 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $900/Night
7 Nights - US $6,298
House
- Boston
- ·
- High Street Hill
- 0.14 mi to center
6 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $2,613/Night
7 Nights - US $18,288
Apartment
- Boston
- ·
- Griggs Park
- 0.15 mi to center
4 Bedrooms
4 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,541/Night
7 Nights - US $10,790
Wheelchair Accessible Holiday Homes in Dudley Square
Over 1533+ Wheelchair Accessible Villas and Holiday Homes in or Near Dudley Square
Condo
- Boston
- ·
- Downtown Boston
- 0.24 mi to center
10.0Exceptional
(54 Reviews)
1 Bedroom
1 Bath
4 Guests
951 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $683/Night
7 Nights - US $4,780
Apartment
- Boston
- ·
- East Cambridge
- 0.40 mi to center
8.0Excellent
(1 Review)
5 Bedrooms
4 Baths
13 Guests
1054.86 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $143/Night
7 Nights - US $1,001
Bed & Breakfast
- Boston
- ·
- Back Bay East
- 0.19 mi to center
9.4Exceptional
(1003 Reviews)
1 Bedroom
1 Bath
- Internet
- Child Friendly
Wheelchair Accessible
Accessibility
US $309/Night
7 Nights - US $2,165
Apartment
- Boston
- ·
- Theatre District
- 0.06 mi to center
10.0Exceptional
(39 Reviews)
1 Bedroom
1 Bath
4 Guests
953 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $572/Night
7 Nights - US $4,004
Apartment
- Boston
- ·
- North Brookline
- 0.32 mi to center
7.8Very Good
(46 Reviews)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $481/Night
7 Nights - US $3,367
Condo
- Boston
- ·
- Boston Financial District
- 0.16 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $149/Night
7 Nights - US $1,042
Condo
- Boston
- ·
- Fenway–Kenmore
- 0.55 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
3 Guests
1200 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $259/Night
7 Nights - US $1,815
Apartment
- Boston
- ·
- D Street - West Broadway
- 0.85 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
743 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $433/Night
7 Nights - US $3,029
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
1368 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $364/Night
7 Nights - US $2,548
Dudley Square Villas, Airbnb and Holiday Homes Under $200
Over 637+ Dudley Square Private Villas, Airbnb and Holiday Homes Under $200
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $164/Night
7 Nights - US $1,151
Apartment
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
5 Guests
602.78 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $166/Night
7 Nights - US $1,161
House
- Boston
- ·
- Prudential - St. Botolph
- 0.16 mi to center
9.2Exceptional
(2010 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $155/Night
7 Nights - US $1,086
New
Condo
2 Bedrooms
1 Bath
4 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
US $154/Night
7 Nights - US $1,076
Bed & Breakfast
- Boston
- ·
- Dorchester
- 1.67 mi to center
9.5Exceptional
(35 Reviews)
5 Bedrooms
5 Baths
14 Guests
- Oceanfront
Skiing- Fireplace/Heating
- Ocean View
US $145/Night
7 Nights - US $1,016
House
- Boston
- ·
- Highland Park
- 0.30 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $138/Night
7 Nights - US $966
Apartment
- Boston
- ·
- Fort Point
- 0.27 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $130/Night
7 Nights - US $910
Apartment
- Boston
- ·
- Mission Hill
- 0.02 mi to center
9.8Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $169/Night
7 Nights - US $1,184
Apartment
- Boston
- ·
- Jones Hill
- 0.05 mi to center
9.4Exceptional
(113 Reviews)
1 Bedroom
1 Bath
3 Guests
530 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $170/Night
7 Nights - US $1,187
Instantly Bookable Villa Rentals in Dudley Square
Over 2148+ Instantly Bookable Private Villas in or Near Dudley Square
Apartment
- Boston
- ·
- Jamaica Plain
- 0.34 mi to center
10.0Exceptional
(126 Reviews)
2 Bedrooms
2 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $345/Night
7 Nights - US $2,414
Apartment
- Massachusetts
- ·
- Boston
- 0.83 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $496/Night
7 Nights - US $3,475
Condo
10.0Exceptional
(104 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $663/Night
7 Nights - US $4,638
Apartment
10.0Exceptional
(103 Reviews)
1 Bedroom
1 Bath
2 Guests
476 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $370/Night
7 Nights - US $2,591
Condo
10.0Exceptional
(97 Reviews)
1 Bedroom
1 Bath
2 Guests
911 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $470/Night
7 Nights - US $3,288
Apartment
10.0Exceptional
(87 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $650/Night
7 Nights - US $4,553
Apartment
10.0Exceptional
(52 Reviews)
1 Bedroom
1 Bath
2 Guests
580 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $639/Night
7 Nights - US $4,474
Condo
- Boston
- ·
- Columbus Park - Andrew Square
- 0.41 mi to center
10.0Exceptional
(52 Reviews)
2 Bedrooms
2 Baths
9 Guests
900 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $603/Night
7 Nights - US $4,224
Apartment
- Boston
- ·
- Dudley - Brunswick King
- 0.60 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $358/Night
7 Nights - US $2,508
Book a Last Minute Place to Stay in Dudley Square
About Dudley Square Vacation Rentals
Discover over 3525 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 530.32 ft², with prices averaging US $482 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 | 2523 |
| Vacation Homes | 441 |
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!
- Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area
- 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
- Charming House In Downtown Boston, Nearby Attractions, Parking & Free WiFi
- Stunning South End/Back Bay Penthouse!
- City's Hippest Neighborhood. n
- Chic South End Studio With Patio
- Great South End/Back Bay location, 1 bed condo near T station
- Beautiful Boston Brownstone!
- Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
How many pickleball-ready properties have private pools in Dudley Square?
Discover 39 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 wd nr groceries BOS-1022
- Stunning Rooftop Apartment & Garden Deck
- Kendall Square 1BR w Concierge Gym nr MIT BOS-716
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.
- Historic 2 floor Apt in Boston w/outdoor deck!
- Luxury 3BR 2BA Boston Penthouse
- Homestay Near Downtown Boston
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 3525 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 | 111 |
| Washington Park Vacation Rentals in Boston, Massachusetts | 31 |
| Dudley - Brunswick King Vacation Rentals in Boston, Massachusetts | 3141 |
People Also Ask
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