Chester Vacation Rentals, Houses & More


1 - 2 of 2

View larger map

Areas near Chester

Don't let other travelers get your favorite vacation rental. You're so close to securing your perfect getaway. Book today.

8
1 / 73

Connecticut Retreat: a magical hide-away

  • 2
  • 6
  • 3 nights min

$150

Details

1 / 49

Great rentals within 30 miles that match your search

1 / 26

Peace Barn in the heart of the CT River Valley

  • 4
  • 10
  • 2 nights min

$192

Details

5
1 / 17

Stay at The Old Sindelar Farm

  • 3
  • 8
  • 1 night min

$120

Details

1 / 21

Beautiful Solar-Powered Yurt at The Sanctuary

  • 1
  • 2
  • 1 night min

$90

Details

1 / 22

Carriage House

  • 2
  • 6
  • 2 nights min

$400

Details

2
1 / 15

Laurel Cottage

  • 2
  • 4
  • 2 nights min

$300

Details

1 / 9

Private 2 Bdrm Cottage, Walk 2 Beach & Riverfront!

  • 2
  • 5
  • Min stay varies

$260

Details

1 / 10

Private 2 Bedroom Cottage - Walk to Beach & River

  • 2
  • 5
  • 7 nights min

$229

Details

1 / 50

Enjoy a unique experience at this beautiful historic New England large property

  • 5
  • 14
  • 2 nights min

$600

Details

1 / 17

Cozy Artist decorated Cottage, walk to beach, pets Ok, exceptional environment

  • 2
  • 6
  • 1 night min

$190

Details

1 / 5

Home available for Academic Monthly or Summer week

  • 2
  • 8
  • 7 nights min

$172

Details

1 / 10

Steps Away from Private Beach

  • 3
  • 6
  • 7 nights min

$257

Details

1 / 12

Luxury Waterfront Home

  • 4
  • 9
  • 3 nights min

$425

Details

1 / 13

Soundview - Beach House - Private Patio and Beach Across the Street

  • 4
  • 10
  • Min stay varies

$349

Details

1 / 5

The Beach Retreat Cottage

  • 3
  • 6
  • Min stay varies

$275

Details

1
1 / 17

9 ROOM WATERFRONT SUMMER COTTAGE (WITH 6 BEDROOMS) FOR RENT ON PRIVATE BEACH

  • 6
  • 10
  • 7 nights min

$172

Details

1
1 / 8

Cornfield Point Beachfront Small Cottage

  • 1
  • 4
  • 7 nights min

$111

Details

1 / 21

Cornfield Point Beachfront Cottage

  • 3
  • 8
  • 7 nights min

$365

Details

5
1 / 17

Sweet Shoreline Madison summer cottage for rent

  • 1
  • 4
  • 7 nights min

$85

Details

1 / 27

Perfect Estate and Location For Your Connecticut the Best

  • 5
  • 14
  • Min stay varies

$749

Details

1 / 12

Spacious studio near beach

  • Studio
  • 3
  • 1 night min

$70

Details

1 / 17

Weekly Summer Beach Rental

  • 4
  • 12
  • 7 nights min

$286

Details

1 / 31

NEW! 3BR Old Lyme Cottage - Steps from the Beach!

  • 3
  • 6
  • Min stay varies

$140

Details

1 / 38

Stunning Waterfront Estate on Connecticut River

  • 5
  • 10
  • Min stay varies

$375

Details

1 / 12

Pail and Shovel Inn 3 bedrm 2 bath Saturday to Saturday in season Weekly rental

  • 3
  • 7
  • 7 nights min

$265

Details

1 / 32

Surrounded By Nature

  • 4
  • 8
  • Min stay varies

$400

Details

1
1 / 21

East Hampton lakefront lakehouse

  • 4
  • 8
  • Min stay varies

$250

Details

1 / 5

Cottage One

  • 1
  • 2
  • 7 nights min

$123

Details

1 / 8

Cottage 2

  • 1
  • 4
  • 7 nights min

$123

Details

2
1 / 21

Spectacular Lakefront Home

  • 4
  • 8
  • Min stay varies

$300

Details

1
1 / 36

Lakeside Ferns - Lake Pocotopaug's Exclusive Vacation Home

  • 3
  • 8
  • Min stay varies

$275

Details

14
1 / 21

The Sun, Sand and Relaxation at Hand! Direct Lakefront, Perfect for 2

  • 1
  • 3
  • Min stay varies

$175

Details

1 / 24

New! Lakefront 1BR Cottage w/ Private Beach & Dock!

  • 1
  • 2
  • Min stay varies

$145

Details

1
1 / 25

White Sandy Beach at your Door

  • 4
  • 11
  • 7 nights min

$569

Details

1 / 49

Lakeside Cottage on Oxoboxo Lake

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 9

3 BR Charming CT shore Beach House at Black Point

  • 3
  • 7
  • 7 nights min

$200

Details

1 / 23

Walk to the town green, beach is 5 mins, dogs welcome.

  • 4
  • 8
  • 2 nights min

$350

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more