Resorts Space Shelter Island
Shelter Island
2 guests

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2

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Shelter Island

Oct 21 - Oct 22 ·
2 guests

Shelter Island Vacation Rentals

Shelter Island
2 guests

Adults:

2

Children:

0

Child’s age:

Navigation

1. Shelter Island Retreat W/ Outdoor Pool!

2. Sandpoint By Rove Travel - 6Br Family Home With Pool

3. King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

4. Fancy Studio Private Entrance

Cheap Shelter Island Vacation Rentals

5. Riverside Retreat-Waterfront Walkout Apartment

6. Downtown New Haven, Spacious Stay By Yale - Ao Destinations

7. The Pines Men-Only Stay

Pet Friendly Vacation Rentals Shelter Island New York State

8. Villa Signor

9. The Cliffside Resort Condominiums

10. Private Apt King Suite, L.I, Ny-Hamptons To Nyc

Best Shelter Island Vacation Rentals

  • Great deal
  • Beach access
Shelter Island Retreat W/ Outdoor Pool! Shelter Island Retreat W/ Outdoor Pool!

Shelter Island Retreat W/ Outdoor Pool!

78 S Ram Island Dr
5.1 km (3.1 mi) from city center
465
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Fitness centre
  • Outdoor swimming pool
10
1 reviews

Shelter Island Retreat W/ Outdoor Pool!

5.1 km (3.1 mi) from city center
465
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Flat-screen TV
  • Fitness centre
  • Outdoor swimming pool

Shelter Island Retreat W/ Outdoor Pool!

10
1 reviews
  • Top location
  • Beach access
Sandpoint By Rove Travel - 6Br Family Home With Pool Sandpoint By Rove Travel - 6Br Family Home With Pool

Sandpoint By Rove Travel - 6Br Family Home With Pool

Brander Parkway 13
2.7 km (1.7 mi) from city center
359
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool
10
1 reviews

Sandpoint By Rove Travel - 6Br Family Home With Pool

2.7 km (1.7 mi) from city center
359
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Outdoor swimming pool

Sandpoint By Rove Travel - 6Br Family Home With Pool

10
1 reviews

Vacation rentals near Shelter Island

  • Best-rated
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

239 Williams Street
38.0 km (23.6 mi) from Shelter Island
17
  • Shared kitchen
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tea and coffee facilities
  • Heating
9.6
115 reviews
~ US$140 / night

King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

38.0 km (23.6 mi) from Shelter Island
17
  • Shared kitchen
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Tea and coffee facilities
  • Heating

King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

9.6
115 reviews
From US$ 140 / night

Cheap Shelter Island Vacation Rentals

Fancy Studio Private Entrance Fancy Studio Private Entrance

Fancy Studio Private Entrance

28 Ormond Avenue
62.3 km (38.7 mi) from Shelter Island
215
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio
9.3
72 reviews
~ US$105 / night

Fancy Studio Private Entrance

62.3 km (38.7 mi) from Shelter Island
215
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Fancy Studio Private Entrance

9.3
72 reviews
From US$ 105 / night
Riverside Retreat-Waterfront Walkout Apartment Riverside Retreat-Waterfront Walkout Apartment

Riverside Retreat-Waterfront Walkout Apartment

622 Military Highway
40.9 km (25.4 mi) from Shelter Island
84
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Terrace
9.5
82 reviews
~ US$286 / night

Riverside Retreat-Waterfront Walkout Apartment

40.9 km (25.4 mi) from Shelter Island
84
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Terrace

Riverside Retreat-Waterfront Walkout Apartment

9.5
82 reviews
From US$ 286 / night
Downtown New Haven, Spacious Stay By Yale - Ao Destinations Downtown New Haven, Spacious Stay By Yale - Ao Destinations

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

32 Elm Street
55.6 km (34.5 mi) from Shelter Island
  • Car park
    Charges may apply
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating
8.8
192 reviews
~ US$117 / night

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

55.6 km (34.5 mi) from Shelter Island
  • Car park
    Charges may apply
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

8.8
192 reviews
From US$ 117 / night

Pet Friendly Vacation Rentals Shelter Island New York State

  • Beach access
The Pines Men-Only Stay The Pines Men-Only Stay

The Pines Men-Only Stay

488 Tarpon Walk
75.3 km (46.8 mi) from Shelter Island
  • VIP check-in/ -out
  • Air conditioning
  • Fitness centre
  • Saltwater pool
  • Heated swimming pool
  • Outdoor swimming pool
9.8
82 reviews
~ US$300 / night

The Pines Men-Only Stay

75.3 km (46.8 mi) from Shelter Island
  • VIP check-in/ -out
  • Air conditioning
  • Fitness centre
  • Saltwater pool
  • Heated swimming pool
  • Outdoor swimming pool

The Pines Men-Only Stay

9.8
82 reviews
From US$ 300 / night
Villa Signor Villa Signor

Villa Signor

311 Old Pond Lane
52.3 km (32.5 mi) from Shelter Island
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Steam room
  • Outdoor swimming pool
9.1
103 reviews
~ US$236 / night

Villa Signor

52.3 km (32.5 mi) from Shelter Island
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Steam room
  • Outdoor swimming pool

Villa Signor

9.1
103 reviews
From US$ 236 / night
  • Guest favorite
  • Private beach
The Cliffside Resort Condominiums The Cliffside Resort Condominiums

The Cliffside Resort Condominiums

61475 Route 48
5.6 km (3.5 mi) from Shelter Island
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Outdoor swimming pool
9.2
221 reviews
~ US$513 / night

The Cliffside Resort Condominiums

5.6 km (3.5 mi) from Shelter Island
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Laundry
  • Outdoor swimming pool

The Cliffside Resort Condominiums

9.2
221 reviews
From US$ 513 / night

Shelter Island Vacation Rentals Oceanfront

Private Apt King Suite, L.I, Ny-Hamptons To Nyc Private Apt King Suite, L.I, Ny-Hamptons To Nyc

Private Apt King Suite, L.I, Ny-Hamptons To Nyc

1 Martin Street
58.3 km (36.2 mi) from Shelter Island
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Tea and coffee facilities
9.3
52 reviews
~ US$123 / night

Private Apt King Suite, L.I, Ny-Hamptons To Nyc

58.3 km (36.2 mi) from Shelter Island
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Luggage storage
  • Tea and coffee facilities

Private Apt King Suite, L.I, Ny-Hamptons To Nyc

9.3
52 reviews
From US$ 123 / night
Historic Peaceful Apartment Historic Peaceful Apartment

Historic Peaceful Apartment

105 Newhall Street 1
57.2 km (35.5 mi) from Shelter Island
11
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Skiing
  • Garden area
8.7
65 reviews
~ US$123 / night

Historic Peaceful Apartment

57.2 km (35.5 mi) from Shelter Island
11
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Skiing
  • Garden area

Historic Peaceful Apartment

8.7
65 reviews
From US$ 123 / night
New! Updated Mystic Home W/ Sauna, Hot Tub & Deck New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

156 Dartmouth Dr.
44.9 km (27.9 mi) from Shelter Island
144
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Sauna
  • Terrace
10
17 reviews
~ US$310 / night

New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

44.9 km (27.9 mi) from Shelter Island
144
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Sauna
  • Terrace

New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

10
17 reviews
From US$ 310 / night

Shelter Island Vacation Rentals with Private Pool

  • Private beach
Cozy Garden Apartment Along The Shoreline Cozy Garden Apartment Along The Shoreline

Cozy Garden Apartment Along The Shoreline

14 Charles St
35.7 km (22.2 mi) from Shelter Island
400
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun loungers
9.2
45 reviews
~ US$202 / night

Cozy Garden Apartment Along The Shoreline

35.7 km (22.2 mi) from Shelter Island
400
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun loungers

Cozy Garden Apartment Along The Shoreline

9.2
45 reviews
From US$ 202 / night
Hyatus Luxury Residences City Crossing Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

9 Tower Lane
55.7 km (34.6 mi) from Shelter Island
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Fitness centre
  • Rooftop pool
9
88 reviews
~ US$289 / night

Hyatus Luxury Residences City Crossing

55.7 km (34.6 mi) from Shelter Island
  • BBQ facilities
  • Free parking
  • 24-hour security
  • Air conditioning
  • Fitness centre
  • Rooftop pool

Hyatus Luxury Residences City Crossing

9
88 reviews
From US$ 289 / night
Beautiful Studio Apartment In Historic House Beautiful Studio Apartment In Historic House

Beautiful Studio Apartment In Historic House

105 Newhall Street
57.2 km (35.5 mi) from Shelter Island
9
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area
8.5
74 reviews
~ US$175 / night

Beautiful Studio Apartment In Historic House

57.2 km (35.5 mi) from Shelter Island
9
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

Beautiful Studio Apartment In Historic House

8.5
74 reviews
From US$ 175 / night
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed

Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed

656 Orange Street
55.7 km (34.6 mi) from Shelter Island
139
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Laundry
9.4
30 reviews
~ US$326 / night

Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed

55.7 km (34.6 mi) from Shelter Island
139
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Laundry

Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed

9.4
30 reviews
From US$ 326 / night
Historic Essex Home W/ Large Yard Near Downtown! Historic Essex Home W/ Large Yard Near Downtown!

Historic Essex Home W/ Large Yard Near Downtown!

73 West Avenue
32.0 km (19.9 mi) from Shelter Island
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Heating
  • Spa & wellness centre
  • Terrace
9.4
14 reviews
~ US$261 / night

Historic Essex Home W/ Large Yard Near Downtown!

32.0 km (19.9 mi) from Shelter Island
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Ironing facilities
  • Heating
  • Spa & wellness centre
  • Terrace

Historic Essex Home W/ Large Yard Near Downtown!

9.4
14 reviews
From US$ 261 / night
Charming Old Saybrook Cottage < 1 Mi To Beach Charming Old Saybrook Cottage < 1 Mi To Beach

Charming Old Saybrook Cottage < 1 Mi To Beach

7 Fenwood Pkwy
22.6 km (14.0 mi) from Shelter Island
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Ironing facilities
10
2 reviews
~ US$221 / night

Charming Old Saybrook Cottage < 1 Mi To Beach

22.6 km (14.0 mi) from Shelter Island
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Ironing facilities

Charming Old Saybrook Cottage < 1 Mi To Beach

10
2 reviews
From US$ 221 / night

Are you in a hurry?

Here is a quick list of Vacation Rentals in Shelter Island, selected based on their rating

Name of hotel Accommodation Rating Price, $
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

9.6 / 10

(115 Reviews)

 From 140$
Fancy Studio Private Entrance

9.3 / 10

(72 Reviews)

 From 105$
Riverside Retreat-Waterfront Walkout Apartment

9.5 / 10

(82 Reviews)

 From 286$
Downtown New Haven, Spacious Stay By Yale - Ao Destinations

8.8 / 10

(192 Reviews)

 From 117$
The Pines Men-Only Stay

9.8 / 10

(82 Reviews)

 From 300$

Location