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Chester Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
49 rentals in Chester.
Charming Chester Retreat- Near Village Center, vacation rental in Chester
Charming Chester Retreat- Near Village Center, vacation rental in Chester
Charming Chester Retreat- Near Village Center, vacation rental in Chester

Charming Chester Retreat- Near Village Center

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester
Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester
Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester

Stunning Artisan Waterfall Escape [Walk to Downtown]

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Millhouse Downtown Chester, vacation rental in Chester
The Millhouse Downtown Chester, vacation rental in Chester
The Millhouse Downtown Chester, vacation rental in Chester

The Millhouse Downtown Chester

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tuscan Villa in Chester CT, vacation rental in Chester
Tuscan Villa in Chester CT, vacation rental in Chester
Tuscan Villa in Chester CT, vacation rental in Chester

Tuscan Villa in Chester CT

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Chester match all your filters:
Charming 2 Bedroom Guest House in Essex, CT, vacation rental in Chester
Charming 2 Bedroom Guest House in Essex, CT, vacation rental in Chester
Charming 2 Bedroom Guest House in Essex, CT, vacation rental in Chester

Charming 2 Bedroom Guest House in Essex, CT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Downtown Essex Apartment - Steps to River!, vacation rental in Chester
Downtown Essex Apartment - Steps to River!, vacation rental in Chester
Downtown Essex Apartment - Steps to River!, vacation rental in Chester

Downtown Essex Apartment - Steps to River!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Winter at the Haddam House, vacation rental in Chester
Winter at the Haddam House, vacation rental in Chester
Winter at the Haddam House, vacation rental in Chester

Winter at the Haddam House

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New England Colonial home with fabulous Connecticut River views!!, vacation rental in Chester
New England Colonial home with fabulous Connecticut River views!!, vacation rental in Chester
New England Colonial home with fabulous Connecticut River views!!, vacation rental in Chester

New England Colonial home with fabulous Connecticut River views!!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning, peaceful and private home, vacation rental in Chester
Stunning, peaceful and private home, vacation rental in Chester
Stunning, peaceful and private home, vacation rental in Chester

Stunning, peaceful and private home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxurious living on a bucolic alpaca farm, vacation rental in Chester
Luxurious living on a bucolic alpaca farm, vacation rental in Chester
Luxurious living on a bucolic alpaca farm, vacation rental in Chester

Luxurious living on a bucolic alpaca farm

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Essex Home w/ Large Yard Near Downtown!, vacation rental in Chester
Historic Essex Home w/ Large Yard Near Downtown!, vacation rental in Chester
Historic Essex Home w/ Large Yard Near Downtown!, vacation rental in Chester

Historic Essex Home w/ Large Yard Near Downtown!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious 1-Bedroom Apartment surrounded by Woods, vacation rental in Chester
Spacious 1-Bedroom Apartment surrounded by Woods, vacation rental in Chester
Spacious 1-Bedroom Apartment surrounded by Woods, vacation rental in Chester

Spacious 1-Bedroom Apartment surrounded by Woods

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cheerful, private cottage in Essex village., vacation rental in Chester
Cheerful, private cottage in Essex village., vacation rental in Chester
Cheerful, private cottage in Essex village., vacation rental in Chester

Cheerful, private cottage in Essex village.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bucolic Carriage House In Beautiful Lyme CT, vacation rental in Chester
Bucolic Carriage House In Beautiful Lyme CT, vacation rental in Chester
Bucolic Carriage House In Beautiful Lyme CT, vacation rental in Chester

Bucolic Carriage House In Beautiful Lyme CT

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Apartment in Antique Home on Second Floor in East Haddam, CT, vacation rental in Chester
Cozy Apartment in Antique Home on Second Floor in East Haddam, CT, vacation rental in Chester
Cozy Apartment in Antique Home on Second Floor in East Haddam, CT, vacation rental in Chester

Cozy Apartment in Antique Home on Second Floor in East Haddam, CT

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Cozy Yacht with Marina Views, vacation rental in Chester
Cozy Yacht with Marina Views, vacation rental in Chester
Cozy Yacht with Marina Views, vacation rental in Chester

Cozy Yacht with Marina Views

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic, vacation rental in Chester
PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic, vacation rental in Chester
PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic, vacation rental in Chester

PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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East Haddam Country Loft......, vacation rental in Chester
East Haddam Country Loft......, vacation rental in Chester
East Haddam Country Loft......, vacation rental in Chester

East Haddam Country Loft......

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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New inside and Out!  Beautiful Lake Front Home, vacation rental in Chester
New inside and Out!  Beautiful Lake Front Home, vacation rental in Chester
New inside and Out!  Beautiful Lake Front Home, vacation rental in Chester

New inside and Out! Beautiful Lake Front Home

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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NEW!!! On VBRO! CT Shoreline Beach Diamond!, vacation rental in Chester
NEW!!! On VBRO! CT Shoreline Beach Diamond!, vacation rental in Chester
NEW!!! On VBRO! CT Shoreline Beach Diamond!, vacation rental in Chester

NEW!!! On VBRO! CT Shoreline Beach Diamond!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Private waterfront home in Historic in Essex CT, vacation rental in Chester
Private waterfront home in Historic in Essex CT, vacation rental in Chester
Private waterfront home in Historic in Essex CT, vacation rental in Chester

Private waterfront home in Historic in Essex CT

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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The perfect New England getaway only a 10 minute walk to downtown!, vacation rental in Chester
The perfect New England getaway only a 10 minute walk to downtown!, vacation rental in Chester
The perfect New England getaway only a 10 minute walk to downtown!, vacation rental in Chester

The perfect New England getaway only a 10 minute walk to downtown!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Storybook Cottage, vacation rental in Chester
Storybook Cottage, vacation rental in Chester
Storybook Cottage, vacation rental in Chester

Storybook Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Renovated Barn, Sidewalk Stroll into Essex Village & Marina, vacation rental in Chester
Renovated Barn, Sidewalk Stroll into Essex Village & Marina, vacation rental in Chester
Renovated Barn, Sidewalk Stroll into Essex Village & Marina, vacation rental in Chester

Renovated Barn, Sidewalk Stroll into Essex Village & Marina

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Luxurious country get away at Flat Rock Farm with alpaca as your neighbors, vacation rental in Chester
Luxurious country get away at Flat Rock Farm with alpaca as your neighbors, vacation rental in Chester
Luxurious country get away at Flat Rock Farm with alpaca as your neighbors, vacation rental in Chester

Luxurious country get away at Flat Rock Farm with alpaca as your neighbors

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cottage with Roger’s Lake views and access., vacation rental in Chester
Cottage with Roger’s Lake views and access., vacation rental in Chester
Cottage with Roger’s Lake views and access., vacation rental in Chester

Cottage with Roger’s Lake views and access.

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Essex Village home within walking distance to downtown., vacation rental in Chester
Essex Village home within walking distance to downtown., vacation rental in Chester
Essex Village home within walking distance to downtown., vacation rental in Chester

Essex Village home within walking distance to downtown.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Sanctuary on the Pond, vacation rental in Chester
Historic Sanctuary on the Pond, vacation rental in Chester
Historic Sanctuary on the Pond, vacation rental in Chester

Historic Sanctuary on the Pond

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Beautiful Period Intact Victorian Apartment in East Haddam, CT, vacation rental in Chester
Beautiful Period Intact Victorian Apartment in East Haddam, CT, vacation rental in Chester
Beautiful Period Intact Victorian Apartment in East Haddam, CT, vacation rental in Chester

Beautiful Period Intact Victorian Apartment in East Haddam, CT

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger, vacation rental in Chester
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger, vacation rental in Chester
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger, vacation rental in Chester

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Rental Home
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful/Relaxing Lakehouse-Sleeps 8-Large Deck with Furniture-Family Friendly, vacation rental in Chester
Beautiful/Relaxing Lakehouse-Sleeps 8-Large Deck with Furniture-Family Friendly, vacation rental in Chester
Beautiful/Relaxing Lakehouse-Sleeps 8-Large Deck with Furniture-Family Friendly, vacation rental in Chester

Beautiful/Relaxing Lakehouse-Sleeps 8-Large Deck with Furniture-Family Friendly

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views, vacation rental in Chester
Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views, vacation rental in Chester
Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views, vacation rental in Chester

Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spectacular Home with Deep Water Dock, vacation rental in Chester
Spectacular Home with Deep Water Dock, vacation rental in Chester
Spectacular Home with Deep Water Dock, vacation rental in Chester

Spectacular Home with Deep Water Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stroll to beach at charming, historical, rustic home w/expansive yard & pool., vacation rental in Chester
Stroll to beach at charming, historical, rustic home w/expansive yard & pool., vacation rental in Chester
Stroll to beach at charming, historical, rustic home w/expansive yard & pool., vacation rental in Chester

Stroll to beach at charming, historical, rustic home w/expansive yard & pool.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern 70s Architectural Marvel - ★★★ Water and Hillside Views, vacation rental in Chester
Modern 70s Architectural Marvel - ★★★ Water and Hillside Views, vacation rental in Chester
Modern 70s Architectural Marvel - ★★★ Water and Hillside Views, vacation rental in Chester

Modern 70s Architectural Marvel - ★★★ Water and Hillside Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Downtown Old Saybrook Oasis, vacation rental in Chester
Downtown Old Saybrook Oasis, vacation rental in Chester
Downtown Old Saybrook Oasis, vacation rental in Chester

Downtown Old Saybrook Oasis

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Home with Endless Charm | Relax, Entertain, Enjoy!, vacation rental in Chester
Home with Endless Charm | Relax, Entertain, Enjoy!, vacation rental in Chester
Home with Endless Charm | Relax, Entertain, Enjoy!, vacation rental in Chester

Home with Endless Charm | Relax, Entertain, Enjoy!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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River and Sunset views!, vacation rental in Chester
River and Sunset views!, vacation rental in Chester
River and Sunset views!, vacation rental in Chester

River and Sunset views!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Near Hartford - 2 Hours from NYC, vacation rental in Chester
Near Hartford - 2 Hours from NYC, vacation rental in Chester
Near Hartford - 2 Hours from NYC, vacation rental in Chester

Near Hartford - 2 Hours from NYC

Rental Home
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
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5 Bedroom Country Home w. Forest Views - ideal for enjoying the fall foliage!, vacation rental in Chester
5 Bedroom Country Home w. Forest Views - ideal for enjoying the fall foliage!, vacation rental in Chester
5 Bedroom Country Home w. Forest Views - ideal for enjoying the fall foliage!, vacation rental in Chester

5 Bedroom Country Home w. Forest Views - ideal for enjoying the fall foliage!

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Fantastic pool home in park-like setting on Connecticut Shore, vacation rental in Chester
Fantastic pool home in park-like setting on Connecticut Shore, vacation rental in Chester
Fantastic pool home in park-like setting on Connecticut Shore, vacation rental in Chester

Fantastic pool home in park-like setting on Connecticut Shore

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!, vacation rental in Chester
Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!, vacation rental in Chester
Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!, vacation rental in Chester

Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Peace Barn in the heart of the CT River Valley, vacation rental in Chester
Peace Barn in the heart of the CT River Valley, vacation rental in Chester
Peace Barn in the heart of the CT River Valley, vacation rental in Chester

Peace Barn in the heart of the CT River Valley

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Secluded Family escape w/ pool & jacuzzi, vacation rental in Chester
Secluded Family escape w/ pool & jacuzzi, vacation rental in Chester
Secluded Family escape w/ pool & jacuzzi, vacation rental in Chester

Secluded Family escape w/ pool & jacuzzi

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Luxury Enchanted Estate w/ Expansive Views & Private Pool, Hot Tub, Tennis Court, vacation rental in Chester
Luxury Enchanted Estate w/ Expansive Views & Private Pool, Hot Tub, Tennis Court, vacation rental in Chester
Luxury Enchanted Estate w/ Expansive Views & Private Pool, Hot Tub, Tennis Court, vacation rental in Chester

Luxury Enchanted Estate w/ Expansive Views & Private Pool, Hot Tub, Tennis Court

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Mansion on the hill, vacation rental in Chester
Mansion on the hill, vacation rental in Chester
Mansion on the hill, vacation rental in Chester

Mansion on the hill

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private resort style pool, hot tub, cabana bar and fun game room, vacation rental in Chester
Private resort style pool, hot tub, cabana bar and fun game room, vacation rental in Chester
Private resort style pool, hot tub, cabana bar and fun game room, vacation rental in Chester

Private resort style pool, hot tub, cabana bar and fun game room

Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT, vacation rental in Chester
Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT, vacation rental in Chester
Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT, vacation rental in Chester

Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT

Rental Home
9 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Lovely, cozy Cottage on a non working farm in a rural town.  Quiet and private., vacation rental in Chester
Lovely, cozy Cottage on a non working farm in a rural town.  Quiet and private., vacation rental in Chester
Lovely, cozy Cottage on a non working farm in a rural town.  Quiet and private., vacation rental in Chester

Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Showing results 1-49 of 49
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