Best price vacation rentals in Chester, CT, USA • 82 Listings
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Chester, CT, USA Vacation Rentals | 

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5.0 (33)
Tuscan Villa in Chester CT
Up to 6 guests
Airbnb$414
Vrbo$414
Average Nightly Rate
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5.0 (21)
The Millhouse Downtown Chester
Up to 5 guests
Airbnb$229
Vrbo$239
Average Nightly Rate
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5.0 (51)
Winter at The Haddam House
Up to 6 guests
Airbnb$211
Vrbo$211
Average Nightly Rate
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4.9 (8)
Elegant Countryside Estate
Up to 11 guests
Airbnb$1,143
Vrbo$1,143
Average Nightly Rate
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4.5 (15)
Historic Essex Home w/ Large Yard Near Downtown!
Up to 4 guests
Vrbo$166
Airbnb$168
Average Nightly Rate
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5.0 (226)
The Federal Suite at the Wisteria Rest
Up to 3 guests
Airbnb$98
Average Nightly Rate
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5.0 (5)
Private Lake Hideaway Nestled in the Woods
Up to 8 guests
Airbnb$475
Average Nightly Rate

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5.0 (65)
Secluded Family escape w/ pool & jacuzzi
Up to 11 guests
Airbnb$342
Average Nightly Rate
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5.0 (67)
The Nest
Up to 2 guests
Airbnb$121
Average Nightly Rate

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5.0 (7)
Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.
Up to 4 guests
Vrbo$250
Average Nightly Rate
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5.0 (145)
Loft apartment, deck and great water view
Up to 3 guests
Airbnb$117
Average Nightly Rate
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5.0 (8)
Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT
Up to 21 guests
Vrbo$875
Average Nightly Rate
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5.0 (165)
Cottage overlooking the CT river
Up to 2 guests
Airbnb$105
Average Nightly Rate
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5.0 (56)
Peaceful quiet retreat amidst gardens and woods
Up to 2 guests
Airbnb$70
Average Nightly Rate
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5.0 (46)
Modern Unique Riverview Hillside Home ★★★Views!
Up to 7 guests
Airbnb$345
Average Nightly Rate
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5.0 (361)
Unique, fun riverfront cottage
Up to 4 guests
Airbnb$123
Average Nightly Rate
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5.0 (88)
Beautiful + Re-imagined Modern Farmhouse
Up to 8 guests
Airbnb$400
Average Nightly Rate
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5.0 (270)
Unique apartment, former contemporary art gallery.
Up to 5 guests
Airbnb$129
Average Nightly Rate
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5.0 (71)
Charming 1806 farm house close to the CT River.
Up to 9 guests
Airbnb$295
Average Nightly Rate
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5.0 (29)
Private Cottage Retreat with Pool
Up to 4 guests
Airbnb$300
Average Nightly Rate
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5.0 (73)
SHABBY CHIC RETREAT
Up to 4 guests
Airbnb$225
Average Nightly Rate
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5.0 (199)
Modern Luxurious CT Country Home
Up to 6 guests
Airbnb$395
Average Nightly Rate
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5.0 (164)
Old Saybrook ensuite near CT River
Up to 2 guests
Airbnb$96
Average Nightly Rate
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5.0 (71)
Early 1900s Log Cabin at Rogers Lake - Suite Style
Up to 3 guests
Airbnb$225
Average Nightly Rate
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5.0 (47)
Birdsong - Relaxation, Activities And Culture In Picturesque Shoreline Town
Up to 2 guests
Vrbo$150
Average Nightly Rate
  1. United States
  2. Connecticut
  3. Chester Vacation Rental Price Comparison

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