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Chester Rentals

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64 Houses

Jennings Perch! Waterfront Cottage close to all!

Chester house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$295

Great rentals within 20 miles that match your search

Direct Waterfront Home - Enjoy all summer long

Old Saybrook house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,184

Direct oceanfront pristine home, Niantic Bay, sunrises, private beach,retreat

Niantic house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$321

Direct beachfront pristine home w/Views like a cruise ship for great vacation

Niantic house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$338

Niantic Beach House

Niantic house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$339

Private 2 Bedroom Cottage - Walk to Beach & River

Westbrook cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$272

3 BR Charming CT shore Beach House at Black Point

Niantic house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$237

Marina Point Villas at Saybrook Point

Old Saybrook villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$947

Historic Granite House in Scenic Jordan Village

Waterford manor house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,540

Luxury Villa at the Norwich Inn and Spa

Norwich villa

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$196

$500 off 2020 book by 6/1/20 CT Victorian Lakefront Mansion Truly Memorable

East Haddam house

7 bedrooms / 4 bathrooms / sleeps 22

“We can't wait to come again!!” Wanted to Thank you for a "Truly Memorable" time. Our entire family want to return to this magical place. We swam, fished, canoed, played volleyball,you name it someone was ready. My wife enjoyed the hammock and balconies to watch everything going on. We played golf nearby, went to a show at the Goodspeed Opera house and enjoyed dinners together on the porch and a wonderful brunch in the glorious dining room that fit everyone. Looking forward to next year!!

Responds fast! avg. 3 hours 47 minutes

Price per night from

$828

Spacious studio near beach

Madison studio

Studio / 1 bathroom / sleeps 3

Price per night from

$83

Victorian Seasons one bedroom duplex farmhouse

East Marion farmhouse

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$415

Newly remodeled 1891 Queen Anne Victorian mansion

Wallingford b&b

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$219

Quaint CT Shore Cottage - Ocean View

Westbrook cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$51

Bright, cheery contemporary ranch style home

Cromwell house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

Brand New Listing Just 1 mile to Downtown and 1.5 miles to the Beach!

Madison house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$267

Villa Signor - European Spa Retreat , near Casinos

Norwich villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$148

Sunny 1910 Beach House, Free Ocean Beach passes, Near Casino

New London house

6 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$440

Clarke's Landing

Middlefield house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$356

Villa Signor! Peaceful Spa Escape w/ nearby Casino

Norwich villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$148

Steps to beach 4bd 2 bth Sleeps 14

Clinton house

3 bedrooms / 2 bathrooms / sleeps 14

Responds fast! avg. 2 hours 16 minutes

Price per night from

$356

Executive Townhouse

Meriden townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$203

Spacious, centrally located three bedroom town home

Cromwell townhouse

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$128

North Fork House with Private Beach Access

East Marion house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 31 minutes

Price per night from

$354

Cottage By The Sea

Clinton cottage

6 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$271

Bright & clean summer rental plus beach pass two blocks from ocean beach

New London house

2 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 15 minutes

Price per night from

$178

Unique English Country Cottage

East Marion cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$470

Victorian Seasons 1 bedroom Carriage House Duplex

East Marion apartment

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$382

Beautiful French Country Cottage

East Marion cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$470

Waterfront w/ Dock on Long Island Sound!

Waterford house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$351

Surrounded By Nature

Guilford house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 7 minutes

Price per night from

$292

Luxurious living on a bucolic alpaca farm

Lyme house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$234

Elegant Meadowbrook Estate for Family Gatherings, Retreats and Special Events

Marlborough manor house

9 bedrooms / 12 bathrooms / sleeps 22

Price per night from

$4,200

Betty's Boat House

Middlefield house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 54 minutes

Price per night from

$146

Dream house vacation on the Long Island Sound

Orient house

5 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 56 minutes

Price per night from

$467

East Hampton lakefront lakehouse

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$261

Pristine Norwich Inn & Spa Villa Near Casinos

Norwich apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$210

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rentals in Chester

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