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97 Houses

12

Spacious studio near beach

Connecticut / Madison

Madison studio

Studio 3 1 night min

  • Studio
  • sleeps 3
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$70

Price per night from

$70

Great rentals within 20 miles that match your search

Distance approx 10.96 km from Madison

29

Old Saybrook Cottage w/Fire Pit - Walk to Beach!

Connecticut / Old Saybrook

Old Saybrook cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$160

Responds fast!
avg. 55 minutes

Price per night from

$160

Distance approx 4.75 km from Madison

24

NEW! Quiet Clinton House Steps to Private Beaches!

Connecticut / Clinton

Clinton house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$175

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$175

Distance approx 5.28 km from Madison

41

New Luxury Waterfront Home

Connecticut / Clinton

Clinton house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$497

Responds fast!
avg. 1 hour 44 minutes

Price per night from

$497

Distance approx 16.8 km from Madison

(5) Excellent 

44

Victorian Seasons Stirling

North Fork / Greenport

Greenport house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 mi
  • Child Friendly
  • Car not necessary

Price per night from

$747

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$747

Distance approx 15.04 km from Madison

(1) Excellent 

22

Little House By the Sea

Connecticut / New Haven

New Haven house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$274

Price per night from

$274

Distance approx 19.25 km from Madison

24

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island / Shelter Island Heights

Shelter Island Heights cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$384

Responds fast!
avg. 55 minutes

Price per night from

$384

Distance approx 17.06 km from Madison

(4) Excellent 

23

Beautiful French Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$399

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$399

Distance approx 16.81 km from Madison

13

Remodeled Greenport Farmhouse

North Fork / Greenport

Greenport farmhouse

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$424

Price per night from

$424

Distance approx 13.34 km from Madison

(10) Excellent 

19

Jamaica Court Cottage

Connecticut / New Haven

New Haven house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly
“Very nice!” We stayed 2 weeks in this beautiful house near the see. The owner is a fantastic host, attentive but never intrusive. Very quiet neighborhood. Perfect for a family with 2 kids. Good location. Great place to stay!!
…see more

Price per night from

$67

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$67

Distance approx 19.25 km from Madison

26

Luxurious ‘Shelter Island Hideaway’ w/ Pool!

Hamptons / Shelter Island

Shelter Island house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$495

Responds fast!
avg. 2 hours 21 minutes

Price per night from

$495

Distance approx 17.13 km from Madison

(1) Very Good 

24

Greenport Home w/Furnished Patio - Walk Downtown!

North Fork / Greenport

Greenport house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$259

Responds fast!
avg. 55 minutes

Price per night from

$259

Distance approx 17.27 km from Madison

12

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

Connecticut / Old Lyme

Old Lyme house

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$263

Price per night from

$263

Distance approx 19.41 km from Madison

24

Dream house vacation on the Long Island Sound

North Fork / Orient

Orient house

5 14 14 nights min

  • 5 bedrooms
  • sleeps 14
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$946

Responds fast!
avg. 2 hours 40 minutes

Price per night from

$946

Distance approx 17.23 km from Madison

26

NEW! Old Lyme Apt. - Walk to Sound View Beach!

Connecticut / Old Lyme

Old Lyme apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$200

Distance approx 17 km from Madison

(4) Excellent 

28

Victorian Seasons one bedroom duplex farmhouse

North Fork / East Marion

East Marion farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$349

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$349

Distance approx 17.32 km from Madison

23

Remodeled Greenport Apartment By Greenport Harbor

North Fork / Greenport

Greenport apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$194

Responds fast!
avg. 55 minutes

Price per night from

$194

Distance approx 18.89 km from Madison

11

Peaceful North Fork Escape - Special Spring and Summer Rates

North Fork / Southold

Southold house

3 5 14 nights min

  • 3 bedrooms
  • sleeps 5
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$249

Price per night from

$249

Distance approx 11.45 km from Madison

32

Ocean front w/ HUGE yard

Connecticut / Old Saybrook

Old Saybrook house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$425

Price per night from

$425

Distance approx 16.28 km from Madison

(6) Excellent 

14

North Fork House with Private Beach Access

North Fork / East Marion

East Marion house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$248

Price per night from

$248

Distance approx 17.01 km from Madison

(2) Excellent 

22

Unique English Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$399

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$399

Distance approx 17.49 km from Madison

34

Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

North Fork / Southold

Southold house

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$348

Price per night from

$348

Distance approx 16.53 km from Madison

(1) Excellent 

14

North Fork Beach House on LI Sound

North Fork / Peconic

Peconic cottage

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$427

Price per night from

$427

Distance approx 19.74 km from Madison

15

Southold Summer Home for rent

North Fork / Southold

Southold house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$464

Price per night from

$464

Distance approx 11.9 km from Madison

12

Waterfront beach bungalow attached but private apartment

Connecticut / Branford

Branford apartment

3 2 nights min

  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$195

Responds fast!
avg. 2 hours 50 minutes

Price per night from

$195

Distance approx 15.48 km from Madison

16

Beautifully Remodeled 4 Bedroom Home in North Haven, CT

Connecticut / North Haven

North Haven house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$149

Price per night from

$149

Distance approx 19.19 km from Madison

25

piece of Heaven

North Fork / Mattituck

Mattituck house

4 14 30 nights min

  • 4 bedrooms
  • sleeps 14
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$1,494

Price per night from

$1,494

Distance approx 18.22 km from Madison

24

NEW! Waterfront Southhold Home w/ Sauna & Dock!

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$350

Responds fast!
avg. 54 minutes

Price per night from

$350

Distance approx 18.6 km from Madison

49

55 Shore

Shelter Island / Shelter Island Heights

Shelter Island Heights villa

6 12 15 nights min

  • 6 bedrooms
  • sleeps 12
  • 15 nights min
  • Ask about children
  • Ask about pets

Price per night from

$3,999

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$3,999

Distance approx 17.32 km from Madison

22

Downtown Greenport Apt w/Porch Near Shelter Island

North Fork / Greenport

Greenport apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$170

Responds fast!
avg. 55 minutes

Price per night from

$170

Distance approx 16.96 km from Madison

24

NEW-East Marion Home 3 Mi to Greenport, by Beaches

North Fork / East Marion

East Marion house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$100

Responds fast!
avg. 55 minutes

Price per night from

$100

Distance approx 17.06 km from Madison

41

LOVELY LARGE RESTORED FARMHOUSE IN BEAUTIFUL EAST MARION

North Fork / East Marion

East Marion house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$648

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$648

Distance approx 18.59 km from Madison

4

Beautiful Luxury Home with Pool in the Heart of Wine Country

North Fork / Cutchogue

Cutchogue house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$697

Price per night from

$697

Distance approx 17.31 km from Madison

19

Southold Contemporary Summer Home Steps from Beach and Vineyard

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$375

Price per night from

$375

Distance approx 18.8 km from Madison

(2) Excellent 

16

Beach House In Wine Country; walk to beach, large sun room, outdoor dining

North Fork / Southold

Southold cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$324

Price per night from

$324

Distance approx 16.24 km from Madison

15

Modern 3 Bedroom 2 Bath Waterfront House with Private Beach!

North Fork / East Marion

East Marion house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$468

Price per night from

$468

Distance approx 19.33 km from Madison

24

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

North Fork / Southold

Southold house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$525

Price per night from

$525

Distance approx 18.88 km from Madison

24

Fabulous Beach Getaway

Hamptons / Shelter Island

Shelter Island house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$650

Price per night from

$650