Cheap Houses for Rent in Shelter Island, NY

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1 Gazon Rd, Shelter Island, NY, 11964
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Beautiful 1 bedroom, 1 bath apartment with adorable kitchenette, separate entrance and large closet/storage space. Utilities & weekly cleaning included. Available now through June; $2,000 per month. (

$2,000/mo

1 bed1 bath— sq ft

1 Gazon Rd, Shelter Island, NY 11964

Car-dependent

3 Lakeview Dr, Shelter Island, NY, 11964
3 Lakeview Dr, Shelter Island, NY, 11964
3 Lakeview Dr, Shelter Island, NY, 11964
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located .6 miles from coveted Wades Beach and Mashomack Preserve. This secluded

$14,000/mo

4 beds2 baths1,720 sq ft

3 Lakeview Dr, Shelter Island, NY 11964

Dogs welcome • Car-dependent • Swimming Pool

5 Bay Ave, Shelter Island, NY, 11964
5 Bay Ave, Shelter Island, NY, 11964
5 Bay Ave, Shelter Island, NY, 11964
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan

$18,000/mo

3 beds3 baths1,675 sq ft

5 Bay Ave, Shelter Island, NY 11964

Parking • A/C • Car-dependent

15 S Cartwright Rd, Shelter Island, NY, 11964
15 S Cartwright Rd, Shelter Island, NY, 11964
15 S Cartwright Rd, Shelter Island, NY, 11964
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Located on the southern side of Shelter Island within close proximity to beaches and boating, this house has been completely renovated with all modern amenities in place. The entry porch leads you int

$30,000/mo

4 beds4 baths3,100 sq ft

15 S Cartwright Rd, Shelter Island, NY 11964

Dogs welcome • Parking • A/C

18 Dickerson Dr, Shelter Island, NY, 11964
18 Dickerson Dr, Shelter Island, NY, 11964
18 Dickerson Dr, Shelter Island, NY, 11964
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Absolutely beautiful, charming, and pristine! Totally renovated home in one of the quietest neighborhoods on Shelter Island. Stunning design and tastefully decorated throughout. Recently renovated a

$40,000/mo

4 beds3.5 baths2,774 sq ft

18 Dickerson Dr, Shelter Island, NY 11964

Parking • A/C • Car-dependent

6 Community Dr, Shelter Island Heights, NY, 11965
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Beautifully renovated and refurnished 3 bedroom 1 bath home with central air, washer/dryer and close to West Neck Bay and community dock to use. Enjoy the spacious yard, deck, fire pit, grill, modern

$40,000/mo

3 beds1 bath1,056 sq ft

6 Community Dr, Shelter Island Heights, NY 11965

Laundry in unit • A/C • Car-dependent

Property at 28 Gardiners Bay Dr, Shelter Island Heights, NY, 11965, 3 beds, 3 baths, [object Object]

$50,000/mo

3 beds3 baths3,000 sq ft

28 Gardiners Bay Dr, Shelter Island Heights, NY 11965

Property at 15 Montclair Ave, Shelter Island, NY, 11964, 6 beds, 4.5 baths, [object Object]

$75,000/mo

6 beds4.5 baths4,600 sq ft

15 Montclair Ave, Shelter Island, NY 11964

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3705 Wells Rd, Peconic, NY, 11958
3705 Wells Rd, Peconic, NY, 11958
3705 Wells Rd, Peconic, NY, 11958
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Fully furnished, tranquil and serene waterfront living on the North Fork set on just shy of an acre. Watch the sunrise from the private pier, dock for your boat, glide around on the kayaks, enjoy the

$3,000/mo

2 beds2 baths1,160 sq ft

3705 Wells Rd, Peconic, NY 11958

Laundry in unit • Parking • Car-dependent

900 Cedar Dr, Southold, NY, 11971
900 Cedar Dr, Southold, NY, 11971
900 Cedar Dr, Southold, NY, 11971
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Looking for the perfect year-round rental on the North Fork? This charming 3-bedroom, 1-bathroom home offers the ideal retreat, whether you're a local resident or seeking a year-round getaway. Nestled

$3,100/mo

3 beds1 bath1,100 sq ft

900 Cedar Dr, Southold, NY 11971

Parking • Car-dependent • Patio/Balcony

3825 S Harbor Rd, Southold, NY, 11971
3825 S Harbor Rd, Southold, NY, 11971
3825 S Harbor Rd, Southold, NY, 11971
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for y

$3,500/mo

2 beds1 bath— sq ft

3825 S Harbor Rd, Southold, NY 11971

Parking • Dishwasher • Car-dependent

45 Baywater Ave, Southold, NY, 11971
45 Baywater Ave, Southold, NY, 11971
45 Baywater Ave, Southold, NY, 11971
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
**off-season rental only. Charming home, originally built in approximately 1905. Main Rd, South onto South Harbor Road, Left on to Baywater Ave. Close proximity all the North Fork has to offer. Down t

$3,500/mo

3 beds2 baths— sq ft

45 Baywater Ave, Southold, NY 11971

Parking • A/C • Car-dependent

400 Diamond Ln, Peconic, NY, 11958
400 Diamond Ln, Peconic, NY, 11958
400 Diamond Ln, Peconic, NY, 11958
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with firepla

$3,500/mo

3 beds1 bath— sq ft

400 Diamond Ln, Peconic, NY 11958

Parking • Car-dependent • Patio/Balcony

870 Stars Rd, East Marion, NY, 11939
870 Stars Rd, East Marion, NY, 11939
870 Stars Rd, East Marion, NY, 11939
ABOUT THIS HOME
Cheap House for Rent in Shelter Island:
Beautiful North Fork home within walking distance to the beach, as well as numerous vineyards, restaurants, and local shops. Upon entering this home, you will enjoy spacious living quarters full of na

$3,500/mo

3 beds3 baths1,500 sq ft

870 Stars Rd, East Marion, NY 11939

Laundry in unit • Parking • A/C

Property at 3400 Youngs Ave, Southold, NY, 11971, 4 beds, 2 baths, [object Object]

$3,500/mo

4 beds2 baths— sq ft

3400 Youngs Ave, Southold, NY 11971

Property at 1975 Youngs Ave, Southold, NY, 11971, 3 beds, 2 baths, [object Object]

$3,500/mo

3 beds2 baths— sq ft

1975 Youngs Ave, Southold, NY 11971

Property at 324 5th Ave, Greenport, NY, 11944, 3 beds, 2 baths, [object Object]

$3,500/mo

3 beds2 baths1,600 sq ft

324 5th Ave, Greenport, NY 11944

Property at 248 5th Ave, Greenport, NY, 11944, 2 beds, 1 bath, [object Object]

$3,800/mo

2 beds1 bath1,306 sq ft

248 5th Ave, Greenport, NY 11944

Property at 5650 N Bayview Rd, Southold, NY, 11971, 5 beds, 2 baths, [object Object]

$3,900/mo

5 beds2 baths2,000 sq ft

5650 N Bayview Rd, Southold, NY 11971

Property at 795 Monsell Ln, Cutchogue, NY, 11935, 3 beds, 2 baths, [object Object]

$4,000/mo

3 beds2 baths1,600 sq ft

795 Monsell Ln, Cutchogue, NY 11935

Property at 2420 Plum Island Ln, Orient, NY, 11957, 3 beds, 1.5 baths, [object Object]

$4,000/mo

3 beds1.5 baths1,600 sq ft

2420 Plum Island Ln, Orient, NY 11957

Property at 25 Oyster Pond Ln, East Hampton, NY, 11937, 3 beds, 2 baths, [object Object]

$4,000/mo

3 beds2 baths— sq ft

25 Oyster Pond Ln, East Hampton, NY 11937

Property at 840 Little Neck Rd, Cutchogue, NY, 11935, 3 beds, 3 baths, [object Object]

$4,200/mo

3 beds3 baths1,300 sq ft

840 Little Neck Rd, Cutchogue, NY 11935

Property at 380 Eds Rd, Southold, NY, 11971, 4 beds, 2 baths, [object Object]

$4,200/mo

4 beds2 baths1,600 sq ft

380 Eds Rd, Southold, NY 11971

Property at 455 W Shore Dr, Southold, NY, 11971, 4 beds, 2.5 baths, [object Object]

$4,200/mo

4 beds2.5 baths1,625 sq ft

455 W Shore Dr, Southold, NY 11971

Property at 8325 Main Rd, East Marion, NY, 11939, 2 beds, 1.5 baths, [object Object]

$4,200/mo

2 beds1.5 baths1,500 sq ft

8325 Main Rd, East Marion, NY 11939

Property at 43 Lincoln St, Sag Harbor, NY, 11963, 1 bed, 1 bath, [object Object]

$4,200/mo

1 bed1 bath650 sq ft

43 Lincoln St, Sag Harbor, NY 11963

Property at 220 Fiddler Ln, Greenport, NY, 11944, 3 beds, 1 bath, [object Object]

$4,500/mo

3 beds1 bath— sq ft

220 Fiddler Ln, Greenport, NY 11944

Based on information submitted to the MLS GRID as of Fri Apr 25 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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