Middletown Vacation Rentals, Houses & More


1 - 38 of 38

View larger map

Areas near Middletown

Great rentals within 30 miles that match your search

1
1 / 20

Bright, cheery contemporary ranch style home

  • 3
  • 6
  • 30 nights min

$135

Details

1 / 38

Stunning Waterfront Estate on Connecticut River

  • 5
  • 10
  • Min stay varies

$375

Details

1 / 32

Clarke's Landing

  • 3
  • 8
  • 2 nights min

$350

Details

1 / 17

Betty's Boat House

  • 2
  • 4
  • Min stay varies

$200

Details

1 / 31

Cozy Space

  • Studio
  • 2
  • 1 night min

$38

Details

1
1 / 21

East Hampton lakefront lakehouse

  • 4
  • 8
  • Min stay varies

$250

Details

1 / 32

Surrounded By Nature

  • 4
  • 8
  • Min stay varies

$400

Details

1
1 / 36

Lakeside Ferns - Lake Pocotopaug's Exclusive Vacation Home

  • 3
  • 8
  • Min stay varies

$275

Details

2
1 / 21

Spectacular Lakefront Home

  • 4
  • 8
  • Min stay varies

$300

Details

2
1 / 15

Laurel Cottage

  • 2
  • 4
  • 2 nights min

$300

Details

1 / 22

Carriage House

  • 2
  • 6
  • 2 nights min

$400

Details

1 / 10

Newly remodeled 1891 Queen Anne Victorian mansion

  • 1
  • 2
  • 1 night min

$185

Details

1 / 21

Beautiful Solar-Powered Yurt at The Sanctuary

  • 1
  • 2
  • 1 night min

$90

Details

8
1 / 73

Connecticut Retreat: a magical hide-away

  • 2
  • 6
  • 3 nights min

$150

Details

5
1 / 17

Stay at The Old Sindelar Farm

  • 3
  • 8
  • 1 night min

$120

Details

1 / 49

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

  • 6
  • 16
  • Min stay varies

$536

Details

1 / 26

Peace Barn in the heart of the CT River Valley

  • 4
  • 10
  • 2 nights min

$192

Details

1 / 10

Royal Master Suite

  • 1
  • 2
  • 1 night min

$90

Details

1 / 13

Mansion & Private 3.5 Acre Estate

  • 4
  • 8
  • Min stay varies

$800

Details

1 / 12

Waterfront beach bungalow attached but private apartment

  • 3
  • 2 nights min

$195

Details

1 / 23

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

  • 4
  • 8
  • 2 nights min

$350

Details

1 / 12

Spacious studio near beach

  • Studio
  • 3
  • 1 night min

$70

Details

5
1 / 17

Sweet Shoreline Madison summer cottage for rent

  • 1
  • 4
  • 7 nights min

$85

Details

1 / 15

Stay Above Our Antique Shop In The Ridgeview Suite

  • 2
  • 4
  • 2 nights min

$280

Details

1 / 30

Tree Fort Suite at Stony Creek Depot

  • 2
  • 4
  • 2 nights min

$225

Details

4
1 / 15

Charming Waterfront Beach Cottage-WOW! Sunsets

  • 4
  • 8
  • 7 nights min

$286

Details

1 / 11

Private Beach 5 bedroom home w/in law apt

  • 5
  • 12
  • 7 nights min

$1000

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 / 13

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

  • 4
  • 10
  • Min stay varies

$429

Details

1
1 / 17

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

  • 6
  • 10
  • 7 nights min

$172

Details

14
1 / 17

Ennis Cottage with private beach on Branford shore

  • 1
  • 2
  • Min stay varies

$125

Details

1 / 12

Luxury Waterfront Home

  • 4
  • 9
  • 3 nights min

$425

Details

1
1 / 17

Walk to private beach from this two bedroom home

  • 2
  • 4
  • Min stay varies

$125

Details

3
1 / 9

Beautiful Vacation Home- Coventry Lake Resort

  • 6
  • 10
  • 2 nights min

$320

Details

1 / 17

Direct Waterfront Renovated Beach House

  • 2
  • 4
  • 3 nights min

$400

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

$191

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