Middletown Vacation Rentals, Houses & More


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Areas near Middletown

Great rentals within 20 miles that match your search

1 / 17

Stay at The Old Sindelar Farm

  • 3
  • 8
  • 1 night min

$120

Details

1 / 35

New! 2BR Moodus Cottage - Walk to Private Beach!

  • 2
  • 6
  • Min stay varies

$115

Details

1 / 21

East Hampton lakefront lakehouse

  • 4
  • 8
  • Min stay varies

$250

Details

1 / 73

Connecticut Retreat: a magical hide-away

  • 2
  • 6
  • 3 nights min

$150

Details

1 / 10

Royal Master Suite

  • 1
  • 2
  • 1 night min

$90

Details

1 / 17

Betty's Boat House

  • 2
  • 4
  • Min stay varies

$201

Details

1 / 10

Newly remodeled 1891 Queen Anne Victorian mansion

  • 1
  • 2
  • 1 night min

$186

Details

1 / 21

Spectacular Lakefront Home

  • 4
  • 8
  • Min stay varies

$300

Details

1 / 36

Lakeside Ferns - Lake Pocotopaug's Exclusive Vacation Home

  • 3
  • 8
  • Min stay varies

$401

Details

1 / 21

Beautiful Solar-Powered Yurt at The Sanctuary

  • 1
  • 2
  • 1 night min

$90

Details

1 / 12

Spacious studio near beach

  • Studio
  • 3
  • 1 night min

$71

Details

1 / 38

Stunning Waterfront Estate on Connecticut River

  • 5
  • 10
  • Min stay varies

$401

Details

1 / 20

Bright, cheery contemporary ranch style home

  • 3
  • 6
  • 30 nights min

$135

Details

1 / 49

Stunning 6 bed, 7 bath home with tennis court, pool, bowling alley, and stage

  • 6
  • 16
  • Min stay varies

$523

Details

1 / 23

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

  • 4
  • 8
  • 2 nights min

$351

Details

1 / 12

Waterfront beach bungalow attached but private apartment

  • 3
  • 2 nights min

$196

Details

1 / 26

Peace Barn in the heart of the CT River Valley

  • 4
  • 10
  • 2 nights min

$192

Details

1 / 32

Surrounded By Nature

  • 4
  • 8
  • Min stay varies

$401

Details

1 / 31

Cozy Space

  • Studio
  • 2
  • 1 night min

$46

Details

1 / 32

Clarke's Landing

  • 3
  • 8
  • 2 nights min

$348

Details

1 / 28

Central Modern Studio

  • 2
  • Min stay varies

$69

Details

1 / 13

Mansion & Private 3.5 Acre Estate

  • 4
  • 8
  • Min stay varies

$800

Details

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