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Winchester Holiday Apartments

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
46 rentals in Winchester.
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93, holiday rental in Winchester

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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House on A+ school area w/AC & W/D, holiday rental in Winchester
House on A+ school area w/AC & W/D, holiday rental in Winchester
House on A+ school area w/AC & W/D, holiday rental in Winchester

House on A+ school area w/AC & W/D

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The following properties within 32 kms of Winchester match all your filters:
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking., holiday rental in Winchester

Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A charming modern suburban 3 bedroom condo close to Boston, holiday rental in Winchester
A charming modern suburban 3 bedroom condo close to Boston, holiday rental in Winchester
A charming modern suburban 3 bedroom condo close to Boston, holiday rental in Winchester

A charming modern suburban 3 bedroom condo close to Boston

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Stoneham Getaway Just Minutes to Boston!, holiday rental in Winchester
Perfect Stoneham Getaway Just Minutes to Boston!, holiday rental in Winchester
Perfect Stoneham Getaway Just Minutes to Boston!, holiday rental in Winchester

Perfect Stoneham Getaway Just Minutes to Boston!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 1 BR private entrance apt commuters dream, holiday rental in Winchester
Charming 1 BR private entrance apt commuters dream, holiday rental in Winchester
Charming 1 BR private entrance apt commuters dream, holiday rental in Winchester

Charming 1 BR private entrance apt commuters dream

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unique loft style garden level studio apartment, holiday rental in Winchester
Unique loft style garden level studio apartment, holiday rental in Winchester
Unique loft style garden level studio apartment, holiday rental in Winchester

Unique loft style garden level studio apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cheerful 1-bedroom New England Ranch, holiday rental in Winchester
Cheerful 1-bedroom New England Ranch, holiday rental in Winchester
Cheerful 1-bedroom New England Ranch, holiday rental in Winchester

Cheerful 1-bedroom New England Ranch

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Located north of Boston/ comfort and relaxation in your home away from home, holiday rental in Winchester
Located north of Boston/ comfort and relaxation in your home away from home, holiday rental in Winchester
Located north of Boston/ comfort and relaxation in your home away from home, holiday rental in Winchester

Located north of Boston/ comfort and relaxation in your home away from home

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 2 bedroom Medford, holiday rental in Winchester
Cozy 2 bedroom Medford, holiday rental in Winchester
Cozy 2 bedroom Medford, holiday rental in Winchester

Cozy 2 bedroom Medford

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Melrose two bedroomer, holiday rental in Winchester
Melrose two bedroomer, holiday rental in Winchester
Melrose two bedroomer, holiday rental in Winchester

Melrose two bedroomer

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet Family Neighborhood, holiday rental in Winchester
Quiet Family Neighborhood, holiday rental in Winchester
Quiet Family Neighborhood, holiday rental in Winchester

Quiet Family Neighborhood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Your Cozy 1 BR Apt & Relaxing Retreat, holiday rental in Winchester
Your Cozy 1 BR Apt & Relaxing Retreat, holiday rental in Winchester
Your Cozy 1 BR Apt & Relaxing Retreat, holiday rental in Winchester

Your Cozy 1 BR Apt & Relaxing Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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★Modern Studio-Private Entrance,Washer+Dryer★, holiday rental in Winchester
★Modern Studio-Private Entrance,Washer+Dryer★, holiday rental in Winchester
★Modern Studio-Private Entrance,Washer+Dryer★, holiday rental in Winchester

★Modern Studio-Private Entrance,Washer+Dryer★

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stylish Studio - ✓Sanitized ✓Private ✓Spotless, holiday rental in Winchester
Stylish Studio - ✓Sanitized ✓Private ✓Spotless, holiday rental in Winchester
Stylish Studio - ✓Sanitized ✓Private ✓Spotless, holiday rental in Winchester

Stylish Studio - ✓Sanitized ✓Private ✓Spotless

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, holiday rental in Winchester
Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, holiday rental in Winchester
Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston, holiday rental in Winchester

Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming 2 bedroom Townhome w/private office suite, holiday rental in Winchester
Charming 2 bedroom Townhome w/private office suite, holiday rental in Winchester
Charming 2 bedroom Townhome w/private office suite, holiday rental in Winchester

Charming 2 bedroom Townhome w/private office suite

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Modern Two Bedroom Condo - Near Boston, holiday rental in Winchester
Modern Two Bedroom Condo - Near Boston, holiday rental in Winchester
Modern Two Bedroom Condo - Near Boston, holiday rental in Winchester

Modern Two Bedroom Condo - Near Boston

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, holiday rental in Winchester
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, holiday rental in Winchester
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!, holiday rental in Winchester

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Unique Cathedral Ceiling Condo W/D, Parking, holiday rental in Winchester
Unique Cathedral Ceiling Condo W/D, Parking, holiday rental in Winchester
Unique Cathedral Ceiling Condo W/D, Parking, holiday rental in Winchester

Unique Cathedral Ceiling Condo W/D, Parking

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Home away from home for work or graduate school., holiday rental in Winchester
Home away from home for work or graduate school., holiday rental in Winchester
Home away from home for work or graduate school., holiday rental in Winchester

Home away from home for work or graduate school.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester
Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!, holiday rental in Winchester

Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern Three Bedroom Condo - Near Boston, holiday rental in Winchester
Modern Three Bedroom Condo - Near Boston, holiday rental in Winchester
Modern Three Bedroom Condo - Near Boston, holiday rental in Winchester

Modern Three Bedroom Condo - Near Boston

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Designer Style 3Br, King Bed, W/D,Parking,Spotless, holiday rental in Winchester
Designer Style 3Br, King Bed, W/D,Parking,Spotless, holiday rental in Winchester
Designer Style 3Br, King Bed, W/D,Parking,Spotless, holiday rental in Winchester

Designer Style 3Br, King Bed, W/D,Parking,Spotless

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, holiday rental in Winchester
Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, holiday rental in Winchester
Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking, holiday rental in Winchester

Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Home in Woburn - Family + Pet Friendly!, holiday rental in Winchester
Home in Woburn - Family + Pet Friendly!, holiday rental in Winchester
Home in Woburn - Family + Pet Friendly!, holiday rental in Winchester

Home in Woburn - Family + Pet Friendly!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New 5B3B Single Family  with Central AC, holiday rental in Winchester
New 5B3B Single Family  with Central AC, holiday rental in Winchester
New 5B3B Single Family  with Central AC, holiday rental in Winchester

New 5B3B Single Family with Central AC

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury home minutes from downtown, casino, and Tufts university, holiday rental in Winchester
Luxury home minutes from downtown, casino, and Tufts university, holiday rental in Winchester
Luxury home minutes from downtown, casino, and Tufts university, holiday rental in Winchester

Luxury home minutes from downtown, casino, and Tufts university

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Cozy Lexington MA Home, Spacious, Backyard, Pet & Child Friendly, Free Parking, holiday rental in Winchester
Cozy Lexington MA Home, Spacious, Backyard, Pet & Child Friendly, Free Parking, holiday rental in Winchester
Cozy Lexington MA Home, Spacious, Backyard, Pet & Child Friendly, Free Parking, holiday rental in Winchester

Cozy Lexington MA Home, Spacious, Backyard, Pet & Child Friendly, Free Parking

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford, holiday rental in Winchester
597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford, holiday rental in Winchester
597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford, holiday rental in Winchester

597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford

Condo/Apartment
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester

Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chic Queen size bedroom with AC, WiFi in Serene Medford next to Beautiful parks, holiday rental in Winchester
Chic Queen size bedroom with AC, WiFi in Serene Medford next to Beautiful parks, holiday rental in Winchester
Chic Queen size bedroom with AC, WiFi in Serene Medford next to Beautiful parks, holiday rental in Winchester

Chic Queen size bedroom with AC, WiFi in Serene Medford next to Beautiful parks

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester
Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking, holiday rental in Winchester

Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy 4-bedroom house in superb Woburn with WiFi, AC - 16 mins to Boston, holiday rental in Winchester
Cozy 4-bedroom house in superb Woburn with WiFi, AC - 16 mins to Boston, holiday rental in Winchester
Cozy 4-bedroom house in superb Woburn with WiFi, AC - 16 mins to Boston, holiday rental in Winchester

Cozy 4-bedroom house in superb Woburn with WiFi, AC - 16 mins to Boston

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk, holiday rental in Winchester
ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk, holiday rental in Winchester
ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk, holiday rental in Winchester

ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Funky and cozy home ! A little bit of everything for everyone., holiday rental in Winchester
Funky and cozy home ! A little bit of everything for everyone., holiday rental in Winchester
Funky and cozy home ! A little bit of everything for everyone., holiday rental in Winchester

Funky and cozy home ! A little bit of everything for everyone.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Bright and Spacious Sleek Studio w/Private Entrance, W/D & Parking, holiday rental in Winchester
Bright and Spacious Sleek Studio w/Private Entrance, W/D & Parking, holiday rental in Winchester
Bright and Spacious Sleek Studio w/Private Entrance, W/D & Parking, holiday rental in Winchester

Bright and Spacious Sleek Studio w/Private Entrance, W/D & Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Near Tufts & Boston 2BR w/ Office & Peloton, holiday rental in Winchester
Modern Near Tufts & Boston 2BR w/ Office & Peloton, holiday rental in Winchester
Modern Near Tufts & Boston 2BR w/ Office & Peloton, holiday rental in Winchester

Modern Near Tufts & Boston 2BR w/ Office & Peloton

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway, holiday rental in Winchester
Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway, holiday rental in Winchester
Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway, holiday rental in Winchester

Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Tufts 2br w/ Standing Desk & Home Theater, holiday rental in Winchester
Tufts 2br w/ Standing Desk & Home Theater, holiday rental in Winchester
Tufts 2br w/ Standing Desk & Home Theater, holiday rental in Winchester

Tufts 2br w/ Standing Desk & Home Theater

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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5 Mi to TD Garden: Quiet Medford Getaway!, holiday rental in Winchester
5 Mi to TD Garden: Quiet Medford Getaway!, holiday rental in Winchester
5 Mi to TD Garden: Quiet Medford Getaway!, holiday rental in Winchester

5 Mi to TD Garden: Quiet Medford Getaway!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Urban Haven, holiday rental in Winchester
Stunning Urban Haven, holiday rental in Winchester
Stunning Urban Haven, holiday rental in Winchester

Stunning Urban Haven

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Self Contain Basement Apartment Close to Boston in a Serene Environment, holiday rental in Winchester
Cozy Self Contain Basement Apartment Close to Boston in a Serene Environment, holiday rental in Winchester
Cozy Self Contain Basement Apartment Close to Boston in a Serene Environment, holiday rental in Winchester

Cozy Self Contain Basement Apartment Close to Boston in a Serene Environment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Queen Anne Victorian in Excellent Location, 3 bedrms, office, WIFI&More, holiday rental in Winchester
Charming Queen Anne Victorian in Excellent Location, 3 bedrms, office, WIFI&More, holiday rental in Winchester
Charming Queen Anne Victorian in Excellent Location, 3 bedrms, office, WIFI&More, holiday rental in Winchester

Charming Queen Anne Victorian in Excellent Location, 3 bedrms, office, WIFI&More

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater., holiday rental in Winchester
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater., holiday rental in Winchester
Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater., holiday rental in Winchester

Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Enchanting Hidden Door Escape, holiday rental in Winchester
Enchanting Hidden Door Escape, holiday rental in Winchester
Enchanting Hidden Door Escape, holiday rental in Winchester

Enchanting Hidden Door Escape

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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